Diisopropylethylamine → 4-(Cyclopropylamino)-N-(2-methyl-5-(4-morpholino-3-(trifluoromethyl)benzamido)phenyl)thieno pyrimidine-7-carboxamide

4-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid (23 mg, 0.10 mmol) was dissolved in dimethylformamide 1.0 mL, HATU (76 mg, 0.20 mmol) and N,N-diisopropylethylamine (0.081 mL, 0.47 mmol) was added thereto, and the mixture was stirred at room temperature for 30 minutes. N-(3-amino-4-methylphenyl)-4-morpholino-3-(trifluoromethyl)benzoamide (25 mg, 0.066 mmol) was added to the reaction mixture and subjected to a reaction at 45° C. for 17 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (5 mL) and washed with an aqueous sodium hydrogen carbonate solution (5 mL). The organic layer was washed with brine (5 mL×3), dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated reactant was crystallized using ethyl acetate (1 mL) and n-hexane (10 mL) to obtain the title compound as a bright brown solid (34 mg).

1. customsubjected to a reaction at 45° C. for 17 hours
2. temperatureAfter cooling to room temperature the reaction mixture
3. washwashed with an aqueous sodium hydrogen carbonate solution (5 mL)
4. washThe organic layer was washed with brine (5 mL×3)
5. dry with materialdried with sodium sulfate
6. distillationthe solvent was distilled under reduced pressure
7. customThe concentrated reactant was crystallized

ORD record

ord-25a1b7667b554881ba8c08b1ac5f7a27

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999973B2