ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate → Ethyl 1-(4-(benzyloxycarbonyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-4-chloro-5-methyl-1H-pyrazole-3-carboxylate

HRID 528884

反応式

HRID 528884 の反応式
[Cl:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][NH:5][C:6]=1[CH3:7].F[C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:16][C:15]=1[C:30]([N:32]1[CH2:41][CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33]1)=[O:31]>>[CH2:21]([O:20][C:18]([C:17]1[CH:28]=[CH:29][C:14]([N:5]2[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4]2)=[C:15]([C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[CH:16]=1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

3

反応物 2

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate2 回HCID 71060780Benzyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

生成物 1

HCID 71062209Ethyl 1-(4-(benzyloxycarbonyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-4-chloro-5-methyl-1H-pyrazole-3-carboxylate収率 48.1%

実験手順

Following a procedure analogous to that for the synthesis of Intermediate 1E, ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate (Intermediate 1A, 509 mg, 2.70 mmol) and benzyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (1.00 g, 2.57 mmol) were converted to the title compound (690 mg, 48%). 1H NMR (CDCl3, 1.5:1 mixture of amide rotamers) δ 8.35-8.28 (m, 1H), 8.18 (t, J=1.9 Hz, 1H), 7.76 (d, J=8.4 Hz, 0.5H), 7.70 (d, J=8.4 Hz, 0.5H), 7.50-7.45 (m, 2H), 7.43-7.31 (m, 3H), 7.23-7.07 (m, 3.5H), 6.90 (d, J=7.9 Hz, 0.5H), 5.42 (s, 2H), 4.76-4.54 (m, 1H), 4.47 (s, 1H), 4.16 (q, J=7.0 Hz, 2.5H), 3.64 (br s, 1.5H), 3.13-3.02 (m, 0.5H), 2.81 (t, J=6.1 Hz, 1H), 2.34 (s, 2H), 2.26 (s, 1H), 1.21 (t, J=7.0 Hz, 1H), 1.12 (t, J=7.2 Hz, 2H); MS(ESI+) m/z 558.4 (M+H)+.

出典と根拠

ORDレコード
ord-a9d9c6001e22443eb733a289e33f2752
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

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