Category: 125568-73-2

Adding a certain compound to certain chemical reactions, such as: 125568-73-2, name is Methyl 5-amino-2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 125568-73-2, Quality Control of Methyl 5-amino-2,4-difluorobenzoate

A mixture of methyl 5-amino-2,4-difluoro-benzoate (2, 3.0 g, 0.016 mol) and 2-chloro-N-(2- chloroethyl)ethanamine hydrochloride (3.719 g, 0.021 mol) in diethylene glycol monomethyl ether (12 mL) was heated to 170C for 2.5h. Progress of the reaction was monitored by TLC. Water was added to the reaction mixture and extracted with ethyl acetate. The organic part was discarded. Then pH of the aqueous part was adjusted with sodium bicarbonate and extracted with ethyl acetate. Combined organic part was dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The crude product obtained was purified by column chromatography to afford the product (1.5 g, 29.9%). LCMS (ESI positive ion) m/z: calculated: 256.25; Observed; 257.0 (M+l).

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Reference:
Patent; ITEOS THERAPEUTICS; CROSIGNANI, Stefano; GOMES, Bruno; HOUTHUYS, Erica; (216 pag.)WO2018/178338; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 125568-73-2,Some common heterocyclic compound, 125568-73-2, name is Methyl 5-amino-2,4-difluorobenzoate, molecular formula is C8H7F2NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of methyl 5-amiotano-2,4-diotafluorobenzoate intermediate 19 (5 5 g, 29 5 mmol, 1 equiv) in dichloromethane (100 mL) at -40 0C was treated with pyridine (7 16 mL, 88 6 mmol, 3 0 equiv) and 1 9 M phosgene in toluene (23 3 mL, 44 3 mmol, 1 5 equiv) After 1 5 h, a solution of 1 ,1-diotamethylethyl 4-(butylamiotano)-1-piotaperiotadiotanecarboxylate intermediate 20 (9 1 g, 35 4 mmol, 1 2 equiv) in dichloromethane (50 mL) was added and the reaction was allowed to warm to RT for 18 h The reaction was diluted with dichloromethane, washed with satd aq NaHCO3, dried over Na2SO4, filtered and concentrated to give intermediate 21 (13 1 g, 95% yield) a white solid1H NMR (400 MHz, DMSO-cfe) delta ppm 8 09 (s, 1 H), 7 89 – 7 99 (m, 1 H), 7 42 (t, J=10 62 Hz, 1 H), 3 88 – 3 99 (m, 1 H), 3 85 (s, 3 H), 3 11 – 3 22 (m, 2 H), 2 96 (d, J=12 27 Hz, 2 H), 2 41 – 2 53 (m, 3 H), 1 43 – 1 59 (m, 5 H), 1 21 – 1 35 (m, 2 H), 1 20 (s, 9 H), 0 90 (t, J=I 33 Hz, 3 H) ES-LCMS m/z 468 1 (M-H); Intermediate 291 ,1-diotamethylethyl 4-[[({2,4-diotafluoro-5-[(methyloxy)carbonyl]phenyl}amiotano)carbonyl](3- fluorophenyl)amiotano]-1-piotaperiotadiotanecarboxylateA solution of methyl 5-amiotano-2,4-diotafluorobenzoate intermediate 19 (5 O g, 26 5 mmol, 1 equiv) in dichloromethane (150 mL) at -40 0C was treated with pyridine (6 4 mL, 79 7 mmol, 3 0 equiv) and 1 9 M phosgene in toluene (20 1 mL, 39 8 mmol, 1 5 equiv) After 1 5 h, the reaction was concentrated down and dried under vac The residue was taken up in dichloromethane (150 mL) and 1 ,1-diotamethylethyl 4-[(3-fluorophenyl)amiotano]-1- piperidmecarboxylate intermediate 6 (8 6 g, 29 2 mmol, 1 1 equiv) was added and the reaction was heated to 40 0C 18 h The reaction was diluted with dichloromethane, washed with satd aq NaHCO3, dried over Na2SO4, filtered and concentrated The residue was purified by silica gel flash column chromatography (0 ? 30% ethyl acetate hexanes) to give intermediate 29 (12 6 g, 94% yield) a white solid1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8 65 (dd, J=8 88, 7 78 Hz, 1 H), 744 – 7 55 (m, 1 H), 7 17 – 7 24 (m, 1 H), 7 04 (d, J=I 87 Hz, 1 H), 6 92 – 6 99 (m, 1 H), 6 80 (t, J=10 26 Hz, 1 H), 5 96 (d, J=Z 11 Hz, 1 H), 4 56 – 4 70 (m, 1 H), 4 03 – 4 26 (m, 2 H), 3 80 – 3 92 (m, 3 H), 2 79 (s, 2 H), 1 85 (d, J=13 37 Hz, 2 H), 1 39 (s, 9 H), 1 19 – 1 35 (m, 2 H) ES-LCMS m/z 530 1 (M+Na)

The synthetic route of 125568-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/75960; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics