Ethylamine → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid ethylamide
Reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:6][C:5]2[C:7]([O:20][C:21]3[CH:22]=[C:23]([F:30])[C:24]([C:27]([OH:29])=O)=[N:25][CH:26]=3)=[CH:8][C:9]([C:11](=[O:19])[NH:12][C:13]3[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=3)=[CH:10][C:4]=2[O:3]1.[CH2:32]([NH2:34])[CH3:33]>>[CH2:32]([NH:34][C:27]([C:24]1[C:23]([F:30])=[CH:22][C:21]([O:20][C:7]2[C:5]3[CH2:6][C:2]([CH3:1])([CH3:31])[O:3][C:4]=3[CH:10]=[C:9]([C:11](=[O:19])[NH:12][C:13]3[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=3)[CH:8]=2)=[CH:26][N:25]=1)=[O:29])[CH3:33]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a similar manner as described for Example 176, from 5-[2,2-dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid (176a) and ethyl amine (1.0 mL, 2.0 M solution in THF) to give a white solid (203 mg, 64% yield). 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1 H) 8.12 (d, J=2.02 Hz, 1 H) 7.65 (t, J=5.43 Hz, 1 H) 7.23-7.32 (m, 1 H) 6.96-7.12 (m, 3 H) 6.78 (d, J=2.02 Hz, 1 H) 3.77 (s, 3 H) 3.40-3.58 (m, 2 H) 2.89 (s, 2 H) 1.50 (s, 6 H) 1.26 (t, J=7.20 Hz, 3 H); LCMS for C23H24FN5O4 m/z 454.20 (M+H+); Anal. Calcd. for C23H24FN5O4.0.10 AcOH: C, 60.65; H, 5.35; N, 15.24; Found: C, 60.62; H, 5.36; N, 15.28.
Sources & evidence
- ORD record
- ord-2c444baa8fec4300b41b24616e3ee775
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119624B2
Reaction notes
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