Triethylamine → HCID 178527248, compound

HRID 394743Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.[CH3:20][CH2:21][N:22](CC)CC.ClCC[S:30](Cl)(=[O:32])=[O:31]>C1COCC1.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH:20]=[CH:21][NH:22][SH:30](=[O:32])=[O:31])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (J Med Chem, 1995;38:3482) (0.30 g, 0.95 mmol) in THF (20 mL) under nitrogen was added Et3N (3.5 mol eq., 3.33 mmol, 245 μL), a catalytic amount of DMAP and chloroethanesulfonyl chloride (1.2 mol eq., 1.14 mmol, 119 μL) dropwise. The reaction was stirred at 25° C. for 1 hour and then diluted with saturated NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50). Crystallization from CH2Cl2/hexane gave N-[4-[(3-bromophenyl)amino]-quinazolin-6-yl]vinylsulfonamide (210 mg, 54%) as a cream powder, mp 217° C. (dec).

Workup

extractionextracted with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
customchromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50)
customCrystallization from CH2Cl2/hexane

Sources & evidence

ORD record: ord-362b27af35714b9fa36c65ac4b92269a
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602863B1

Reaction notes

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