Triethylamine → HCID 23537546, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[S:16][C:15]([C:17]([OH:19])=O)=[CH:14][CH:13]=1.C(N(CC)CC)C.C(Cl)(=O)OCC(C)C.[F:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[NH2:43]>O1CCCC1.O>[F:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[NH:43][C:17]([C:15]1[S:16][C:12]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[N:8]=[CH:7][N:6]=2)=[CH:13][CH:14]=1)=[O:19]Participants
7
Procedure
300 mg of 5-(6-bromoquinazolin-4-yl)thiophen-2-carboxylic acid (compound in Production Example 382) was dissolved in 4 mL tetrahydrofuran, then 0.37 mL triethylamine and 0.14 mL isobutyl chlorocarbonate were added thereto under ice-cooling, and the mixture was stirred for 1 hour under nitrogen atmosphere. This mixture was added to a solution of 1.15 g 2,4-difluorophenylamine in 10 mL tetrahydrofuran and stirred at room temperature for 1 hour. Further, the reaction mixture was stirred at 70° C. for 3 hours, then water was added thereto, the reaction mixture was extracted with ethyl acetate, and the solvent was evaporated. The residue was washed with ether to give 171 mg of the title compound as pale yellow crystals.
Workup
- temperatureunder ice-cooling
- stirringstirred at room temperature for 1 hour
- stirringFurther, the reaction mixture was stirred at 70° C. for 3 hours
- extractionthe reaction mixture was extracted with ethyl acetate
- customthe solvent was evaporated
- washThe residue was washed with ether
Sources & evidence
- ORD record
- ord-a33f2b4bd31c4863a209666470456a1f
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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