Triethylamine → HCID 86716055, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](O)=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27][CH2:26]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([N:25]3[CH2:26][CH2:27][CH:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])[CH2:29][CH2:30]3)=[O:22])[C:9]=2[CH3:24])=[CH:6][CH:7]=1Participants
Procedure
To 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1 eq, 200 mg, 0.52 mmol), tert-butyl 4-piperidinylcarbamate (1 eq, 105 mg, 0.052 mmol), and triethylamine (3 eq, 0.22 mL, 1.57 mmol) was added (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1 eq, 232 mg, 0.52 mmol). The reaction was stirred 16 h and then concentrated in vacuo. The crude material was purified by column chromatography 0-100% ethyl acetate/hexanes to yield 277 mg (93%) of desired product. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 11H) 1.95-2.10 (m, 2H) 2.14-2.25 (m, 3H) 2.97 (br. s., 1H) 3.25 (d, J=7.63 Hz, 1H) 3.66-3.82 (m, 1H) 4.31 (d, J=13.37 Hz, 1H) 4.49 (d, J=5.84 Hz, 1H) 4.66 (d, J=13.09 Hz, 1H) 7.03-7.10 (m, 2H) 7.12-7.18 (m, 1H) 7.21-7.34 (m, 3H) 7.45 (d, J=2.07 Hz, 1H); [M+Na]+ 587.4.
Workup
- concentrationconcentrated in vacuo
- customThe crude material was purified by column chromatography 0-100% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-8b6ba287adf646e68a6a779180731b6c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133128B2
Reaction notes
Loading…