Sodium Hydroxide → N-tert-butyl-2-(6-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide
Reaction equation
C(OC[N:9]1[C:13]2=[N:14][CH:15]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][C:23]([C:27]#[N:28])=[CH:24][CH:25]=4)[N:20]([CH3:29])[N:19]=3)[N:17]=[C:12]2[C:11]([C:30](=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:10]1)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1>[C:32]([NH:31][C:30]([C:11]1[C:12]2[C:13](=[N:14][CH:15]=[C:16]([C:18]3[C:26]4[C:21](=[CH:22][C:23]([C:27]#[N:28])=[CH:24][CH:25]=4)[N:20]([CH3:29])[N:19]=3)[N:17]=2)[NH:9][CH:10]=1)=[O:36])([CH3:35])([CH3:34])[CH3:33]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of (7-(tert-butylcarbamoyl)-2-(6-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (80 mg, 0.164 mmol) in THF (5 mL) was added a 15% NaOH aqueous solution (0.5 mL) at room temperature and the reaction mixture stirred for 15 hours. The solvent was evaporated under reduced pressure. The residue was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 15% acetonitrile/75% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 70% acetonitrile/30% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give N-tert-butyl-2-(6-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (45 mg, 74%) as white solid.
Workup
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
- wait15% acetonitrile/75% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 70% acetonitrile/30% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.
Sources & evidence
- ORD record
- ord-369b7de767a34b458a619ec1e6444937
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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