4-(1-Aminocyclopropyl)benzonitrile → N-[1-(4-cyanophenyl)cyclopropyl]-2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide
Reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:21])=[C:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:6]=1[C:7](O)=[O:8].[NH2:22][C:23]1([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1>>[C:30]([C:29]1[CH:28]=[CH:27][C:26]([C:23]2([NH:22][C:7]([C:6]3[C:5]([CH2:10][C:11]4[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=4)=[C:4]([CH3:21])[S:3][C:2]=3[CH3:1])=[O:8])[CH2:25][CH2:24]2)=[CH:33][CH:32]=1)#[N:31]Participants
3
Procedure
2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxylic acid from Example 11, Step 4 (286 mg, 0.910 mmol) was reacted with 4-(1-aminocyclopropyl)benzonitrile from Example 14, Step 1 (144 mg, 0.910 mmol) under conditions similar to Example 1, Step 10. The crude product was purified by Combi Flash chromatography system (2-5% EtOAc/CHCl3 in 20 min.) to afford the desired product as a pale yellow solid.
Workup
- customThe crude product was purified by Combi Flash chromatography system (2-5% EtOAc/CHCl3 in 20 min.)
Sources & evidence
- ORD record
- ord-f63ba648ce7c4e4ea821b8b9d830b2ac
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969394B2
Reaction notes
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