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 1428878Notes

Reaction equation

HRID 1428878 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-bf1c8e410611462481533531473c60bc
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…