Methoxyacetic Acid → HCID 57794565, 화합물

HRID 2099373노트

반응식

HRID 2099373 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[Cl:27][C:28]1[C:29]([F:54])=[C:30]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][C:41]([O:47][C@H:48]4[CH2:53][CH2:52][CH2:51][NH:50][CH2:49]4)=[C:42]([O:45][CH3:46])[CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1.C(N(C(C)C)CC)(C)C.[CH3:64][O:65][CH2:66][C:67](O)=[O:68]>C(Cl)Cl>[Cl:27][C:28]1[C:29]([F:54])=[C:30]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][C:41]([O:47][C@H:48]4[CH2:53][CH2:52][CH2:51][N:50]([C:67](=[O:68])[CH2:66][O:65][CH3:64])[CH2:49]4)=[C:42]([O:45][CH3:46])[CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1

참가 물질

6

반응물 4

HCID 12251Methoxyacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68908613HCID 68908613, 화합물

생성물 1

HCID 57794565HCID 57794565, 화합물수율 80.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

HATU (0.24 g) was added to a solution of N-(3-chloro-2-fluorophenyl)-6-methoxy-7-[(3S)-piperidin-3-yloxy]quinazolin-4-amine dihydrochloride (250 mg), diisopropylethylamine (0.37 ml) and methoxyacetic acid (0.054 g) in methylene chloride (9 ml) and the mixture was stirred at room temperature for 2.5 hours. Methylene chloride (20 ml) was added and the organic layer was washed with aqueous sodium hydroxide (2M, 30 ml) and water (30 ml). The resulting product was purified by flash column chromatography eluting with methanol (3%) and methylene chloride (97%) gave a foam. This was re-precipitated by stirring in diethyl ether (20 ml) to give the title product as a white solid (0.202 g); 1H NMR Spectrum: (DMSO d6 373K) 1.60 (m, 1H), 1.88 (m, 2H), 2.10 (m, 1H), 3.32 (s, 3H), 3.51 (m, 2H), 3.62 (m, 1H), 3.87 (m, 1H), 3.98 (s, 3H), 4.02 (d, J=14 Hz, 1H), 4.12 (d, J=14 Hz, 1H), 4.66 (m, 1H), 7.26 (m, 1H), 7.33 (s, 1H), 7.43 (m, 1H), 7.62 (m, 1H), 7.83 (s, 1H), 8.40 (s, 1H), 9.34 (br s, 1H); Mass Spectrum: (M+H)+ 475.

후처리

  1. washthe organic layer was washed with aqueous sodium hydroxide (2M, 30 ml) and water (30 ml)
  2. customThe resulting product was purified by flash column chromatography
  3. washeluting with methanol (3%) and methylene chloride (97%)
  4. customgave a foam
  5. customThis was re-precipitated
  6. stirringby stirring in diethyl ether (20 ml)

출처 및 근거

ORD 기록
ord-dac002e72e7046bbae25709f96481338
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569577B2

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