4-Chloro-3-(trifluoromethyl)aniline → HCID 53346280, compound

HRID 1465032Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=3[CH3:21])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][C:36]=1[C:42]([F:45])([F:44])[F:43]>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:23]([NH:41][C:38]4[CH:39]=[CH:40][C:35]([Cl:34])=[C:36]([C:42]([F:43])([F:44])[F:45])[CH:37]=4)=[O:25])[CH:17]=[CH:16][C:15]=3[CH3:21])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Amino-N-(5-amino-2-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide (50 mg, 0.167 mmol) obtained in Step 3 of Example 39 was dissolved in anhydrous THF (1 mL), TEA (47 μL, 0.334 mmol) and triphosgene (17 mg, 0.059 mmol) were added thereto at 0° C., and the mixture was stirred for 2 hours. 4-Chloro-3-(trifluoromethyl)benzeneamine (49 mg, 0.251 mmol) was added to the reaction mixture, which was stirred at room temperature for 10 hours. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with brine. The organic layer was dried with MgSO4, filtered and then concentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography (MeOH/DCM=3/97) to obtain the title compound (54 mg, 60%).

Workup

stirringwas stirred at room temperature for 10 hours
washwashed with brine
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting mixture was purified by silica gel chromatography (MeOH/DCM=3/97)

Sources & evidence

ORD record: ord-41522ef909e54fecb09ab6b7f669f1c3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999973B2

Reaction notes

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