Benzoyl chloride → 1-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428874ノート

反応式

HRID 1428874 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28](=[O:38])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH2:39])[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11]>C(Cl)Cl>[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28](=[O:38])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH:39][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11]

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 684879131-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

生成物 1

HCID 684879621-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Benzoyl chloride (81.1 μL, 0.698 mmol) was added dropwise to a solution of 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.200 g, 0.466 mmol), TEA (0.162 mL, 1.16 mmol), and DCM (2.3 mL). The reaction mixture was stirred at room temperature for 1.5 h and was then diluted with DCM (25 mL) and quenched with water (15 mL). The organic layer was washed with water (20 mL) and brine (20 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (10-70% EtOAc/hexanes) to yield the titled compound (0.240 g, 97% yield). MS (ESI/Cl): mass calcd. for C27H31N5O5Si, 533.2; m/z found, 476.2 [M+H−58]+.

後処理

  1. customquenched with water (15 mL)
  2. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by FCC (10-70% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-be7c7556dba14defab04e63697906cf1
出典データセット
uspto-grants-2015_01
特許番号
US08937078B2

反応ノート

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