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 1428874Notes

Reaction equation

HRID 1428874 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-be7c7556dba14defab04e63697906cf1
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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