Triethylamine → HCID 178527248, compound

HRID 1698956Notes

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-b43b553841824300a309324ac43c43cf
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344459B1

Reaction notes

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