tert-butyl 4-(1-(7-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-3-yl)piperidine-1-carboxylate → N-(1-hydroxy-2-methylpropan-2-yl)-2-(3-(piperidin-4-yl)-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246522Notes

Reaction equation

HRID 246522 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([CH:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[N:19]3)[N:16]=2)[N:11]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[CH:10]=1)=[O:8])([CH3:5])[CH3:4]>FC(F)(F)CO>[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[N:19]3)[N:16]=2)[N:11]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:46])([CH3:45])[CH3:47])[CH:10]=1)=[O:8])([CH3:5])[CH3:4]

Participants

3

Reactant 1

HCID 71280186tert-butyl 4-(1-(7-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-3-yl)piperidine-1-carboxylate

Product 1

HCID 71280834N-(1-hydroxy-2-methylpropan-2-yl)-2-(3-(piperidin-4-yl)-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A stirred solution of tert-butyl 4-(1-(7-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-3-yl)piperidine-1-carboxylate (120 mg, 181 μmol) in 2,2,2-trifluoroethanol (2 mL) was heated in a microwave at 150° C. for 4 h. The mixture was concentrated in vacuo and used in the next step without purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customused in the next step without purification

Sources & evidence

ORD record
ord-71b31651759c4cde94762d600ba64915
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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