4-(3-Tert-butyl-5-phenoxycarbonylamino-pyrazol-1-yl)benzoic acid methyl ester → 4-(3-Tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH:15][C:16](OC3C=CC=CC=3)=[O:17])=[CH:13][C:12]([C:25]([CH3:28])([CH3:27])[CH3:26])=[N:11]2)=[CH:6][CH:5]=1.[F:30][C:31]1[CH:36]=[C:35]([O:37][C:38]2[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[CH:39]=2)[CH:34]=[CH:33][C:32]=1[NH2:45]>>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH:15][C:16]([NH:45][C:32]3[CH:33]=[CH:34][C:35]([O:37][C:38]4[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[CH:39]=4)=[CH:36][C:31]=3[F:30])=[O:17])=[CH:13][C:12]([C:25]([CH3:26])([CH3:28])[CH3:27])=[N:11]2)=[CH:6][CH:5]=1Participants
3
Reactant 2
Product 1
Procedure
A solution of 4-(3-tert-butyl-5-phenoxycarbonylamino-pyrazol-1-yl)benzoic acid methyl ester (470 mg, 1.19 mmol) and 2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenylamine (260.69 mg, 1.19 mmol) was stirred at 40° C. overnight. The mixture was cooled to room temperature, and then evaporated at reduced pressure. The residue was purified by MPLC (eluting with 50:50 EtOAc/hexane) to afford the title compound (407 mg, 66%). 1H-NMR (DMSO-d6) δ 8.94 (s, 2H), 8.30 (d, J=5.7 Hz, 1H), 8.09 (m, 3H), 7.71 (d, J=5.7 Hz, 2H), 7.20 (d, J=14.7, 1H), 6.94 (d, J=5.4 Hz, 1H), 6.77 (d, J=2.7 Hz, 1H), 6.72 (d, J=5.4 Hz, 1H), 6.42 (s, 1H), 3.87 (s, 3H), 2.38 (s, 3H), 1.27 (s, 9H); MS LC-MS [M+H]+=518.2, RT=2.94 min.
Workup
- customevaporated at reduced pressure
- customThe residue was purified by MPLC (eluting with 50:50 EtOAc/hexane)
Sources & evidence
- ORD record
- ord-8bd576919de245bb9b8de6836ec10f5e
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207166B2
Reaction notes
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