4-Hydrazinyl-2-(trifluoromethyl)benzonitrile hydrochloride → 2-[4-Cyano-3-(trifluoromethyl)phenyl]-3-cyclopentyl-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid
Reaction equation
[CH:1]1([CH:6]=[C:7]2[C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([C:18]([O:20]C)=[O:19])=[CH:13][CH:14]=3)[O:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH:23]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=1)[NH2:24]>>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:23]2[CH:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]3[CH2:8][O:9][C:10]4[CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=[CH:14][C:15]=4[C:16]3=[N:24]2)=[CH:26][C:27]=1[C:33]([F:34])([F:35])[F:36])#[N:30]Participants
3
Procedure
The title compound was prepared from methyl 3-(cyclopentylmethylene)-4-oxochroman-7-carboxylate (Preparation 31; 286 mg, 1.0 mmol) and 4-hydrazinyl-2-(trifluoromethyl)benzonitrile hydrochloride (Preparation 3; 298 mg, 1.3 mmol) according to Method B and Method C. The title compound was largely present as a mixture of cis and trans diastereomers:
Sources & evidence
- ORD record
- ord-6dd5550dd4fd47eb970d042b703804b7
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781428B2
Reaction notes
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