1-Methyl-3-aminopyrazole → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyrimidine-2-carboxylic acid dimethylamide
Reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.C[O:9][C:10]([C:12]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[N:26][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[N:28][CH:29]=2)[C:15]2[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=2[CH:13]=1)=O>>[CH3:33][N:31]([CH3:32])[C:30]([C:27]1[N:28]=[CH:29][C:24]([O:23][C:21]2[C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=3[CH:13]=[C:12]([C:10](=[O:9])[NH:1][C:2]3[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=3)[CH:22]=2)=[CH:25][N:26]=1)=[O:34]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a similar manner as described for Example 1, from 3-amino-1-methyl-pyrazole (152 mg, 1.56 mmol) and 4-(2-dimethylcarbamoyl-pyrimidin-5-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (164b) (58 mg, 0.16 mmol) to give a white solid (64 mg, 94% yield). 1H NMR (400 MHz, CDCl3) δ 8.96 (s, 1 H) 8.47 (s, 2 H) 7.20-7.34 (m, 1 H) 7.07 (d, J=1.52 Hz, 2 H) 6.76 (d, J=2.02 Hz, 1 H) 3.73 (s, 3 H) 3.14 (s, 3 H) 2.98 (s, 3 H) 2.92 (s, 2 H) 1.49 (s, 6 H); LCMS for C22H24N6O4 m/z 437.00 (M+H+); Anal. Calcd. for C22H24N6O4.0.15 CHCl3: C, 58.55; H, 5.36; N, 18.50; Found: C, 58.59; H, 5.45; N, 18.61.
Sources & evidence
- ORD record
- ord-ca691b08fda64518b4bf30d000ab8bbf
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
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