5-Bromo-3-(1-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one → 5-tert-Butyl-2-(3-(5-(1-ethyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)isoindolin-1-one
Reaction equation
C([O:4][CH2:5][C:6]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=[CH:8][C:7]=1[N:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=2)[C:22]1=[O:34])(=O)C.Br[C:36]1[CH:37]=[C:38]([NH:44][C:45]2[CH:49]=[CH:48][N:47]([CH2:50][CH3:51])[N:46]=2)[C:39](=[O:43])[N:40]([CH3:42])[CH:41]=1>>[C:30]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:34])[N:21]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([C:36]3[CH:37]=[C:38]([NH:44][C:45]4[CH:49]=[CH:48][N:47]([CH2:50][CH3:51])[N:46]=4)[C:39](=[O:43])[N:40]([CH3:42])[CH:41]=3)[C:6]=1[CH2:5][OH:4])[CH2:29]2)([CH3:33])([CH3:31])[CH3:32]Participants
3
Reactant 2
Product 1
Procedure
Following the same general procedure as described for 105, reaction of 103f (556 mg, 1.20 mmol) with 106a (300 mg, 1.00 mmol) gave a 20% (101 mg) yield of 106 as a white solid: mp 175-177° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.07 (s, 1H), 8.01 (d, 1H, J=2.0 Hz), 7.73 (d, 1H, J=7.5 Hz), 7.71 (s, 1H), 7.62 (dd, 1H, J=8.0, 1.0 Hz), 7.52 (d, 1H, J=2.5 Hz), 7.49 (t, 1H, J=7.5 Hz), 7.42 (dd, 1H, J=7.5, 1.0 Hz), 7.36 (dd, 1H, J=7.5, 1.0 Hz), 7.25 (d, 1H, J=2.0 Hz), 6.06 (d, 1H, J=2.0 Hz), 4.94 (s, 2H), 4.89 (t, 1H, J=5.0 Hz), 4.35 (d, 2H, J=5.0 Hz), 3.98 (q, 2H, J=7.5 Hz), 3.58 (s, 3H), 1.37 (s, 9H), 1.31 (t, 3H, J=7.5 Hz); MS (ESI+) m/z 512.3 (M+H).
Sources & evidence
- ORD record
- ord-36c3b2dea12b46bca4b6b232159f50eb
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249123B2
Reaction notes
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