Bis-(1H-imidazol-2-YL)-methanone → (+/-)-3-(7-Methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester

HRID 2099744ノート

反応式

HRID 2099744 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH2:16])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2.[C:18](C1NC=CN=1)(C1NC=CN=1)=[O:19].[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]2=[O:46])[CH2:32][CH2:31]1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:16][C:18]([N:30]1[CH2:31][CH2:32][CH:33]([N:36]2[CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]2=[O:46])[CH2:34][CH2:35]1)=[O:19])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2

参加物

5

反応物 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 58864334methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate

生成物 1

HCID 24862915(+/-)-3-(7-Methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of (±)-2-amino-3-(7-methyl-1H-indazol-5-yl)-propionic acid methyl ester (162.9 mg, 0.698 mmol) in methylene chloride (3 mL) at room temperature was treated with carbonyl diimidazole (113.2 mg, 1 equiv). After 1.5 h at room temperature, 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (161.5 mg, 1 equiv.) was added. The mixture was stirred at room temperature overnight. A white precipitate had formed that was shown to be the desired product. The solvent was evaporated and the residue triturated with methylene chloride. The product was collected by filtration, washed with methylene chloride and dried in vacuo to give a white solid (241.5 mg, 71%). Some product remained in the mother liquors. 1H-NMR (dimethylformamide-d7, 500 MHz) δ 1.75 (4H, m), 2.78 (3H, s), 2.7-3.1 (4H, m), 3.35 (2H, m), 3.86 (3H, s), 4.44 (2H, s), 4.57 (1H, m), 4.72 (1H, m), 7.11 (3H, m), 7.31 (1H, s), 7.34 (2H, m), 7.72 (1H, s), 9.34 (1H, s). Mass spec.: 491.13 (MH)+.

後処理

  1. customA white precipitate had formed

出典と根拠

ORDレコード
ord-d5b8e798a90a472eb688731cb6d8e345
出典データセット
uspto-grants-2009_08
特許番号
US07569578B2

反応ノート

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