1-Methylimidazole → Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate

HRID 1410013ノート

反応式

HRID 1410013 の反応式
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[C:11]3[N:16]=[CH:15][S:14][C:12]=3[N:13]=2)[CH2:4]1.[OH:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[C:38]([O:40][CH3:41])=[O:39])[C:32](O)=[O:33].CCN=C=NCCCN(C)C.CN1C=CN=C1>C(Cl)Cl>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([NH:17][C:10]2[C:11]3[N:16]=[CH:15][S:14][C:12]=3[N:13]=[C:8]([N:5]3[CH2:6][CH2:7][CH:3]([NH:2][C:32]([C:31]4[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:29]([OH:28])[CH:30]=4)=[O:33])[CH2:4]3)[N:9]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

参加物

6

反応物 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 670501783-Hydroxy-4-(methoxycarbonyl)benzoic acidHCID 683792715-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride

生成物 1

HCID 68379322Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate収率 45.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (164 mg, 0.4 mmol), 3-hydroxy-4-(methoxycarbonyl)benzoic acid (78 mg, 0.4 mmol), EDCI (153 mg, 0.8 mmol) and N-methylimidazole (100 mg, 1.2 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography (silica gel, 100% DCM to DCM:MeOH=50:1) to give methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)-2-hydroxybenzoate (100 mg, yield 45%). LC-MS: 551 [M+H]+, tR=1.61 min.

後処理

  1. washThe mixture was washed with water (4 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by column chromatography (silica gel, 100% DCM to DCM:MeOH=50:1)

出典と根拠

ORDレコード
ord-bfe88ea28a324d249477650f3ebb9b8c
出典データセット
uspto-grants-2014_12
特許番号
US08921383B2

反応ノート

読み込み中…