N-methyl-2-pyrrolidone → HCID 67388631、化合物

HRID 905694ノート

反応式

HRID 905694 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]([CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)C(=O)OC(C)(C)C)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.CN1C(=O)CCC1>O>[ClH:1].[ClH:1].[ClH:1].[CH3:15][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=[C:2]([NH:19][C:20]3[CH:42]=[CH:41][C:23]([CH2:24][NH:25][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][O:38][CH2:39][CH2:40]4)=[CH:22][CH:21]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 184608435-Pyrimidinecarboxamide, 2-chloro-4-[(3-methylphenyl)amino]-HCID 67387804Carbamic acid, [(4-aminophenyl)methyl][2-(4-morpholinyl)ethyl]-, 1,1-dimethylethyl ester

生成物 1

HCID 67388631HCID 67388631、化合物収率 70.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

A mixture of 1.0 g of 2-chloro-4-(3-methylanilino)pyrimidine-5-carboxamide, 1.6 g of tert-butyl 4-aminobenzyl(2-morpholin-4-ylethyl)carbamate, 1.33 ml of diisopropylethylamine and 10 ml of NMP was stirred overnight at 130° C. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, the solvent was evaporated, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol). Then, a 750 mg portion of 780 mg of the resulting compound was stirred overnight at room temperature in a mixed solution of 75 ml methanol and 30 ml 6 M hydrochloric acid. The reaction mixture was concentrated, and then the resulting crystals were washed with methanol to obtain 510 mg of 4-[(3-methylphenyl)amino]-2-[(4-{[(2-morpholin-4-ylethyl)amino]methyl}phenyl)amino]pyrimidine-5-carboxamide trihydrochloride as colorless crystals.

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol)
  6. stirringThen, a 750 mg portion of 780 mg of the resulting compound was stirred overnight at room temperature in a mixed solution of 75 ml methanol and 30 ml 6 M hydrochloric acid
  7. concentrationThe reaction mixture was concentrated
  8. washthe resulting crystals were washed with methanol

出典と根拠

ORDレコード
ord-e78bcd652d0344888d2c7663434997c6
出典データセット
uspto-grants-2011_09
特許番号
US08012959B2

反応ノート

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