1-(phenylsulfonyl)-1H-indol-3-ylboronic acid → 2-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol
Reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=1.[C:29]1([S:35]([N:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](B(O)O)=[CH:39]2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH3:11][N:8]1[C:7]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[N:6][C:5]2[C:9]1=[N:10][C:2]([C:40]1[C:41]3[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]([S:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:37])=[O:36])[CH:39]=1)=[N:3][C:4]=2[N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1Participants
Procedure
2-(1-((2-Chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol was reacted with 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid via General Procedure B to give intermediate 2-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol. The intermediate was suspended in MeOH (3 mL) whereupon 3N KOH (0.3 mL) was added and the reaction mixture was heated at 50° C. for several hours until the protecting group was removed. Reverse phase purification gave 115. MS (Q1) 490.3 (M)+. 1H NMR (400 MHz, DMSO) δ 11.46 (s, 1H), 8.67-8.51 (m, 1H), 8.13 (d, 1H), 7.53-7.25 (m, 2H), 7.20-7.07 (m, 2H), 4.27 (s, 4H), 4.02 (s, 1H), 3.84 (s, 3H), 3.76 (dd, 12.2, 4H), 3.69 (s, 2H), 2.88 (d, 2H), 1.97 (t, 2H), 1.66 (d, 2H), 1.21 (dt, 3H), 1.02 (s, 6H)
Sources & evidence
- ORD record
- ord-13c6f9b89a43426cb29c8e6e15a3d145
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158625B2
Reaction notes
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