1-Methyl-3-aminopyrazole → 4-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-2-fluoro-benzoic acid tert-butyl ester
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.[C:8]([O:12][C:13]([C:15]1[CH:35]=[CH:34][C:18]([O:19][C:20]2[C:25]3[CH2:26][C:27]([CH3:30])([CH3:29])[O:28][C:24]=3[CH:23]=[C:22]([C:31](O)=[O:32])[CH:21]=2)=[CH:17][C:16]=1[F:36])=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:8]([O:12][C:13](=[O:14])[C:15]1[CH:35]=[CH:34][C:18]([O:19][C:20]2[C:25]3[CH2:26][C:27]([CH3:29])([CH3:30])[O:28][C:24]=3[CH:23]=[C:22]([C:31](=[O:32])[NH:7][C:4]3[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=3)[CH:21]=2)=[CH:17][C:16]=1[F:36])([CH3:9])([CH3:10])[CH3:11]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a similar manner as described for Example 15 except that the reaction was carried out at 75° C. for 2 hr, from 1-methyl-3-aminopyrazole (892 mg, 9.18 mmol) and 4-(4-tert-butoxycarbonyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (66b) (2.46 g, 6.11 mmol) to give a white solid (1.77 g, 60% yield). 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1 H) 7.87 (t, J=8.59 Hz, 1 H) 7.28 (d, J=2.27 Hz, 1 H) 7.07 (s, 1 H) 7.04 (s, 1 H) 6.79 (d, J=2.02 Hz, 1 H) 6.75 (dd, J=8.84, 2.27 Hz, 1 H) 6.68 (dd, J=11.75, 2.40 Hz, 1H) 3.80 (s, 3 H) 2.87 (s, 2 H) 1.60 (s, 9 H) 1.49 (s, 6H); LCMS for C26H28FN3O5 m/z 505.00 (M+Na)+.
Sources & evidence
- ORD record
- ord-e233e3a23a1d4e0d8fd40af3a5ec15de
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119624B2
Reaction notes
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