3-(N-Isopropylaminocarbonyl)benzeneboronic acid → N-isopropyl-3-(5-(5-methyl-1H-pyrazol-3-ylamino)-2-(trifluoromethyl)imidazo[1,2-c]pyrimidin-7-yl)benzamide
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[N:5]2[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=[C:4]2[CH:3]=1.[CH:22]([NH:25][C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27])([CH3:24])[CH3:23]>>[CH:22]([NH:25][C:26](=[O:27])[C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=3)[N:5]3[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=[C:4]3[CH:3]=2)[CH:33]=1)([CH3:24])[CH3:23]Participants
3
Procedure
Title compound was synthesized from 7-chloro-N-(5-methyl-1H-pyrazol-3-yl)-2-(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-amine and 3-(isopropylcarbamoyl)phenyl boronic acid using the procedure described in Example 278. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=6.57 Hz, 6H) 2.32 (s, 3H) 4.15 (td, J=13.45, 6.69 Hz, 2H) 6.74 (s, 1H) 7.60 (t, J=7.71 Hz, 1H) 7.78 (s, 1H) 7.90 (d, J=7.83 Hz, 1H) 8.27 (d, J=8.08 Hz, 1H) 8.38 (d, J=7.58 Hz, 1H) 8.57 (s, 1H) 9.03 (s, 1H) 10.55 (s, 1H); ESI-MS: m/z calc'd for C21H20F3N7O 443.43; found 444.3 (M+H)+.
Sources & evidence
- ORD record
- ord-61b7ded7916c4c2cb103bb1641ec8044
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713973B2
Reaction notes
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