Isobutanol → 1-(6-isobutoxy-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide
Reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].F[C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([NH:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][N:32]=4)(=[O:29])=[O:28])=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1>CN(C=O)C>[CH2:3]([O:4][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([NH:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][N:32]=4)(=[O:29])=[O:28])=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1)[CH:2]([CH3:5])[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a ice cold solution of 2-methylpropan-1-ol (110 mg, 1.483 mmol) in DMF (1483 μl) was added sodium hydride (59.3 mg, 1.483 mmol) under nitrogen and stirred for 10 min to this was then added a solution of 1-(6-fluoro-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (122 mg, 0.297 mmol) in DMF (1483 μl) and stirred for 16 h slowly raising the temperature to ambient temperature. The reaction mixture was quenched with MeOH, concentrated and purified via reverse phase HPLC (0.1% NH4OH in ACN and water as mobile phase) to obtain 1-(6-isobutoxy-2-methoxypyridin-3-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as light yellow solid (56 mg, 120 mmol, 41% yield). m/z (ESI) 466.2 (M+H)+.
Workup
- stirringstirred for 16 h
- customThe reaction mixture was quenched with MeOH
- concentrationconcentrated
- custompurified via reverse phase HPLC (0.1% NH4OH in ACN and water as mobile phase)
Sources & evidence
- ORD record
- ord-ed65300c380a4e6c81ad82a11ac5cfec
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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