Difluoroacetic acid → HCID 178498370, 화합물

HRID 44548

반응식

HRID 44548 반응식
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:19][CH:20]([F:24])[C:21](O)=O>C1(C)C=CC=CC=1>[F:19][CH:20]([F:24])[C:21]1[NH:1][C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:10][C:11]=2[N:12]=1

참가 물질

4

반응물 2

HCID 9788Difluoroacetic acidHCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate

생성물 1

HCID 178498370HCID 178498370, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of methyl 2,3-diamino-5-morpholinobenzoate (40.16 g, 160 mmol) and 2,2-difluoroacetic acid (46.08 g, 480 mmol) in toluene (500 mL) was stirred at reflux temperature for 15 h. Then the mixture was cooled to room temperature and the solvent was removed in vacuum. The residue was purified by silica gel chromatography eluted with petroleum ether:EtOAc=2:1 to afford the desired product. Then, it was dissolved with EtOAc (2 L) and washed with aqueous NaHCO3 (1 L) and brine (1 L). The organic layer was dried over anhydrous Na2SO4 and concentrated to give the desired product (40.9 g, 82%) as a yellow solid. 1H NMR showed this compound is in a form of tautomeric mixture (major tautomer/minor tautomer=5/1) 1H NMR of the major tautomer (300 MHz, DMSO-d6): δ ppm 3.14 (t, 4H, J=4.8 Hz), 3.78 (t, 4H, J=4.8 Hz), 3.96 (s, 3H), 7.21 (t, 1H, J=52.8 Hz), 7.55 (d, 1H, J=2.4 Hz), 7.65 (d, 1H, J=2.4 Hz), 12.92 (s, 1H); LC-MS: m/e=312 [M+1]+

후처리

  1. temperatureat reflux temperature for 15 h
  2. customthe solvent was removed in vacuum
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with petroleum ether

출처 및 근거

ORD 기록
ord-bb4f66d5fc0e4c1bb4198b86bbfc5930
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541411B2

연결된 노트

불러오는 중…