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

HRID 1428878ノート

反応式

HRID 1428878 の反応式
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:21]2[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:29](=[O:39])[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([NH2:40])[CH:27]=3)[N:22]=2)[CH:20]=1)=[O:15])[CH3:12]>N1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:21]2[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:29](=[O:39])[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([NH:40][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:27]=3)[N:22]=2)[CH:20]=1)=[O:15])[CH3:12]

参加物

4

反応物 2

HCID 7369Benzenesulfonyl 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 684885401-[6-benzenesulfonylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester収率 95%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Benzenesulfonyl chloride (0.131 mL, 1.02 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) in pyridine (2.3 mL). The reaction mixture was stirred for 2 h, then quenched with water (15 mL) and extracted with EtOAc (30 mL). The organic layer was washed with water (15 mL) and brine (15 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (5-50% EtOAc/hexanes) to yield the titled compound (0.253 mg, 95% yield). MS (ESI/Cl): mass calcd. for C26H31N5O6SSi, 569.2; m/z found, 512.1 [M+H−58]+.

後処理

  1. customquenched with water (15 mL)
  2. extractionextracted with EtOAc (30 mL)
  3. washThe organic layer was washed with water (15 mL) and brine (15 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by FCC (5-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-bf1c8e410611462481533531473c60bc
出典データセット
uspto-grants-2015_01
特許番号
US08937078B2

反応ノート

読み込み中…