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

HRID 1428879노트

반응식

HRID 1428879 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19](=[O:29])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:30])[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19](=[O:29])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 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 684886321-[6-benzylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester수율 90.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A vial was charged with 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.250 g, 0.582 mmol), benzaldehyde (59.2 μL, 0.582 mmol), and 4 Å MS (0.25 g). DCE was added (1.9 mL) and the reaction mixture was stirred at room temperature for 18 h. Sodium triacetoxyborohydride (0.308 g, 1.46 mmol) was added and the reaction mixture was stirred for a further 24 h. The reaction was quenched with saturated aqueous sodium bicarbonate (10 mL) and was then extracted with DCM (3×15 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (2-40% EtOAc/hexanes) to yield the titled compound (0.273 g, 90% yield). MS (ESI/Cl): mass calcd. for C27H33N5O4Si, 519.2; m/z found, 520.2 [M+H]+.

후처리

  1. stirringthe reaction mixture was stirred for a further 24 h
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate (10 mL)
  3. extractionwas then extracted with DCM (3×15 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (2-40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-fe063256a10944cebc210734386fab2e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937078B2

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