Triphenylphosphine → (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrile
Reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=2)=[CH:4][CH:3]=[N:2]1.O[C@H:19]([CH3:29])[CH2:20][NH:21]C(=O)OC(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[NH2:21][CH2:20][C@@H:19]([N:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:7]=2)=[N:1]1)[CH3:29]Participants
5
Procedure
The title compound was prepared from 4-(1H-pyrazol-5-yl)-2-(trifluoromethyl)benzonitrile (1.4 g, 5.90 mmol), (R)-tert-butyl 2-hydroxypropylcarbamate (1.03 g, 5.90 mmol), triphenylphosphine (2.32 g, 8.85 mmol) and di-tert-butyl azodicarboxylate (2.04 g, 8.85 mmol) using the method of Example 34(c). Yield 0.429 g. 1H NMR (400 MHz; MeOD): δ 1.52 (d, 3H), 2.98 (dd, 1H), 3.12 (dd, 1H), 4.43 (m, 1H), 6.87 (d, 1H), 7.77 (d, 1H), 7.98 (m, 1H), 8.21 (m, 1H), 8.33 (m, 1H).
Sources & evidence
- ORD record
- ord-c19d9b014b9c4241a2d1e660effa64b6
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
Loading…