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 1428878노트

반응식

HRID 1428878 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-bf1c8e410611462481533531473c60bc
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937078B2

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