Cyclopropaneethanamine → N-(2-Cyclopropylethyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887274

반응식

HRID 1887274 반응식
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=O)=[C:11]([CH3:13])[N:12]=2)[C:4](=[O:17])[CH:3]=1.[CH:18]1([CH2:21][CH2:22][NH2:23])[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][CH2:22][NH:23][C:14]([C:10]2[S:9][C:8]([N:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]3=[O:17])=[N:12][C:11]=2[CH3:13])=[O:16])[CH2:20][CH2:19]1

참가 물질

3

반응물 2

HCID 10240761CyclopropaneethanamineHCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

생성물 1

HCID 54742335N-(2-Cyclopropylethyl)-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide수율 64%

실험 절차

Following the procedure as described in Example 1, making variations only as required to use 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with 2-cyclopropylethanamine, the title compound was obtained as a colorless solid in 64% yield: mp 234-236° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.47 (s, 1H), 8.58 (d, J=8.0 Hz, 1H), 8.16 (t, J=5.6 Hz, 1H), 6.25 (dd, J=8.0, 2.6 Hz, 1H), 5.81 (d, J=2.5 Hz, 1H), 3.26-3.20 (m, 2H), 2.50 (s, 3H), 1.40-1.34 (m, 2H), 0.76-0.59 (m, 1H), 0.39-0.33 (m, 2H), 0.03-0.01 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 167.8, 161.8, 161.6, 153.9, 149.4, 132.6, 124.2, 104.3, 98.0, 39.9, 34.4, 17.4, 9.0, 4.6; MS (ES+) m/z 320.2 (M+1).

출처 및 근거

ORD 기록
ord-20e65636ac34441290d13f1ca5cb70b0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501746B2

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