3-Pyridinemethanamine → (S)-N-(3,4-difluorobenzyl)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 554951

반응식

HRID 554951 반응식
N1C=CC=C(CN)C=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH2:14].[F:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]2[C@@H:29]([CH3:30])[CH2:28][N:27]([C:31]3[S:32][C:33]([C:37](O)=[O:38])=[C:34]([CH3:36])[N:35]=3)[C:26]2=[O:40])=[CH:22][CH:21]=1>>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH:14][C:37]([C:33]1[S:32][C:31]([N:27]2[CH2:28][C@H:29]([CH3:30])[N:25]([CH2:24][C:23]3[CH:41]=[CH:42][C:20]([F:19])=[CH:21][CH:22]=3)[C:26]2=[O:40])=[N:35][C:34]=1[CH3:36])=[O:38]

참가 물질

4

반응물 3

HCID 310183-PyridinemethanamineHCID 1235723,4-DifluorobenzylamineHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

생성물 1

HCID 57919760(S)-N-(3,4-difluorobenzyl)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide수율 74%

실험 절차

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with 3,4-difluorobenzylamine to react with (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as an off-white solid in 74% yield: mp 62-65° C. (diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 8.54 (t, J=5.9 Hz, 1H), 7.44-7.30 (m, 4H), 7.21-7.12 (m, 3H), 4.60 (d, J=15.6 Hz, 1H), 4.35 (d, J=5.9 Hz, 2H), 4.30 (d, J=15.6 Hz, 1H), 4.19 (dd, J=10.0, 9.1 Hz, 1H), 3.80-3.69 (m, 1H), 3.55 (dd, J=10.0, 6.2 Hz, 1H), 2.47 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 161.8, 161.5 (d, 1JC-F=244 Hz), 157.2, 154.9, 151.3, 150.4 (dd, JC-F=66, 13 Hz), 147.1 (dd, JC-F=66, 13 Hz), 137.6 (dd, JC-F=5, 4 Hz), 133.1 (d, 4JC-F=3 Hz), 130.0 (d, 3JC-F=8 Hz), 124.0 (dd, JC-F=7, 3 Hz), 117.6, 117.3 (d, JC-F=17 Hz), 116.3 (d, JC-F=17 Hz), 115.4 (d, 2JC-F=21 Hz), 49.4, 48.6, 43.7, 41.7, 18.4, 17.1; MS (ES+) m/z 474.8 (M+1).

출처 및 근거

ORD 기록
ord-26ce1cc359d2415ca8458d1b907523c9
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049016B2

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