Pipemidic Acid → 8-Ethyl-5-oxo-2-[4-[[3-(trifluoromethyl)phenyl]carbamothioyl]piperazin-1-yl]pyrido[2,3-d]pyrimidine-6-carboxylic acid

HRID 455923

반응식

HRID 455923 반응식
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[S:33])[CH:28]=[CH:29][CH:30]=1.C(N(CC)CC)C>>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:26]=[C:27]([NH:31][C:32]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[N:12]=[CH:13][C:8]4[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:2][CH3:1])[C:9]=4[N:10]=3)[CH2:15][CH2:16]2)=[S:33])[CH:28]=[CH:29][CH:30]=1

참가 물질

4

반응물 3

HCID 4831Pipemidic AcidHCID 8471TriethylamineHCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzene

생성물 1

HCID 15178238-Ethyl-5-oxo-2-[4-[[3-(trifluoromethyl)phenyl]carbamothioyl]piperazin-1-yl]pyrido[2,3-d]pyrimidine-6-carboxylic acid

실험 절차

Pipemidic acid (25 mg, 0.0824 mmol), 3-(trifluoromethyl)phenyl isothiocyanate (12.5 μL, 0.0824 mmol) and triethylamine (23 μL, 0.165 mmol) were used. Purification on silica yielded compound 11 in Table 1, below (31 mg, 75%). 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 8.72 (s, 1H), 7.41-7.35 (m, 1H), 7.29-7.21 (m, 2H), 7.21-7.16 (m, 1H), 4.37 (q, J=7.10 Hz, 2H), 4.27-3.93 (m, 8H), 1.50 (t, J=7.04 Hz, 3H) ppm.

후처리

  1. customPurification on silica yielded compound 11 in Table 1

출처 및 근거

ORD 기록
ord-ee6f65d270004bac92c1d89b050fea72
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497371B2

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