Methyl chloroglyoxylate → (3-(4-Chloro-3-methyl-phenyl)-1-{3-[4-(2-cyano-phenyl)-piperazin-1-yl]-2-hydroxy-propyl}-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-oxo-acetic acid methyl ester

HRID 33588

反応式

HRID 33588 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:11]=3[N:10]([CH2:17][CH:18]([OH:34])[CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=4[C:28]#[N:29])[CH2:22][CH2:21]3)[N:9]=2)=[CH:4][C:3]=1[CH3:35].Cl[C:37](=[O:42])[C:38]([O:40][CH3:41])=[O:39].CO.C(Cl)Cl>C(Cl)Cl>[CH3:41][O:40][C:38](=[O:39])[C:37]([N:14]1[CH2:15][CH2:16][C:11]2[N:10]([CH2:17][CH:18]([OH:34])[CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=4[C:28]#[N:29])[CH2:22][CH2:21]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:35])[CH:4]=3)[C:12]=2[CH2:13]1)=[O:42]

参加物

5

反応物 3

HCID 79846Methyl chloroglyoxylateHCID 179754122-(4-{3-[3-(4-Chloro-3-methyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperazin-1-yl)-benzonitrileHCID 21226129Dichloromethane methanol

生成物 1

HCID 10281649(3-(4-Chloro-3-methyl-phenyl)-1-{3-[4-(2-cyano-phenyl)-piperazin-1-yl]-2-hydroxy-propyl}-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-oxo-acetic acid methyl ester収率 79.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(4-{3-[3-(4-Chloro-3-methyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperazin-1-yl)-benzonitrile (58 mg, 0.118 mmol) was dissolved in CH2Cl2 (0.59 mL) and treated with methyl chlorooxoacetate (16 mg, 0.129 mmol). The reaction mixture was allowed to stir for 18 h at room temperature. Column chromatography (silica, 2-10% MeOH/CH2Cl2) gave (3-(4-chloro-3-methyl-phenyl)-1-{3-[4-(2-cyano-phenyl)-piperazin-1-yl]-2-hydroxy-propyl}-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-oxo-acetic acid methyl ester (54 mg, 79%) as a white solid. MS (electrospray): m/z 577.3 (577.2, calculated for C30H33ClN6O4, [M+H]+). 1H NMR (400 MHz, CDCl3): 7.32-7.62 (m, 5H), 7.14 (t, J=7.6 Hz, 1H), 7.05 (d, J=8.2 Hz, 1H), 4.59-4.80 (m, 3H), 4.12-4.28 (m, 2H), 3.92 (s, 3H), 3.78-3.86 (m, 2H), 3.44-3.60 (m, 5H), 3.15-3.40 (m, 4H), 2.83-3.05 (m, 2H), 2.41 (s, 3H).

出典と根拠

ORDレコード
ord-94e1ed89ff444fd1be60dfad663ad43b
出典データセット
uspto-grants-2008_09
特許番号
US07429591B2

関連ノート

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