Triethylamine → HCID 178527247, compound

HRID 507454Notes

Reaction equation

HRID 507454 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)CC)[CH3:21].N1C=CC=CC=1.CNC.ClCC[S:39](Cl)(=[O:41])=[O:40]>O1CCCC1.C([O-])(O)=O.[Na+]>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH:21]=[CH:20][NH:22][SH:39](=[O:41])=[O:40])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazolineHCID 21954350Dimethylamine pyridine

Product 1

HCID 178527247HCID 178527247, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 7-amino-4-[(3-bromophenyl)-amino]quinazoline (J Med Chem, 1995;38:3482) (500 mg, 1.59 mmol), triethylamine (Et3N) (0.60 mL) and dimethylamine pyridine (DMAP) (catalytic) in tetrahydrofuran (THF) (30 mL) was reacted with chloroethanesulfonyl chloride (1.6 mol eq., 2.54 mmol, 265 μL) at 25° C. for 1 hour, stirred under N2. The reaction mixture was 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-7-yl]vinylsulfonamide (80 mg, 12%) as a cream powder, mp 218° C. decomposes (dec).

Workup

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

Sources & evidence

ORD record
ord-b37420632bf74f4096bb707d1f1d70d7
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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