Sodium Hydroxide → 2-(6-cyano-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246607Notes

Reaction equation

HRID 246607 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:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:10]1)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1>[C:27]([C:23]1[CH:22]=[C:21]2[C:26]([C:18]([C:16]3[N:17]=[C:12]4[C:11]([C:30]([NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[O:37])=[CH:10][NH:9][C:13]4=[N:14][CH:15]=3)=[N:19][N:20]2[CH3:29])=[CH:25][CH:24]=1)#[N:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71280709(2-(6-cyano-1-methyl-1H-indazol-3-yl)-7-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate

Product 1

HCID 712796452-(6-cyano-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-(6-cyano-1-methyl-1H-indazol-3-yl)-7-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)methyl pivalate (45 mg, 0.089 mmol) in 2 mL of THF was added a solution of 10% NaOH (2 mL) at room temperature and the reaction mixture was stirred for 15 hours. The solvent was evaporated under reduced pressure. The residue was diluted with water and adjusted to pH 5-6. The mixture was filtered and the filter cake washed with DMSO (3 mL), MeOH (3 mL) and then dried to give 2-(6-cyano-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (4.5 mg, 12%) as white solid. MS: (M+H)+=390; 1H NMR (300 MHz, DMSO): δ 12.95 (brs, 1H), 9.14 (s, 1H), 8.79 (d, 1H, J=8.1 Hz), 8.54 (s, 1H), 8.42 (s, 1H), 7.91 (s, 1H), 7.62 (d, 1H, J=8.4 Hz), 5.15 (brs, 1H), 4.27 (s, 3H), 3.64 (d, 2H, J=5.4 Hz), 1.47 (s, 6H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe mixture was filtered
  4. washthe filter cake washed with DMSO (3 mL), MeOH (3 mL)
  5. customdried

Sources & evidence

ORD record
ord-402275a52da245d4bc494a31d6934746
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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