tert-butyl 3-((3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-5-(difluoromethoxy)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate → 2-(1-(Azetidin-3-ylmethyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246507Notes

Reaction equation

HRID 246507 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:30][CH:31]4[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]4)[N:18]=3)[N:15]=2)[N:10]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)CO>[NH:33]1[CH2:34][CH:31]([CH2:30][N:19]2[C:20]3[C:25](=[CH:24][C:23]([O:26][CH:27]([F:29])[F:28])=[CH:22][CH:21]=3)[C:17]([C:14]3[N:15]=[C:16]4[C:8]([C:6]([NH:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[CH:9][N:10]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:11]4=[N:12][CH:13]=3)=[N:18]2)[CH2:32]1

Participants

3

Reactant 1

HCID 71280303tert-butyl 3-((3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-5-(difluoromethoxy)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate

Product 1

HCID 712799372-(1-(Azetidin-3-ylmethyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-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 3-((3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-5-(difluoromethoxy)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate (180 mg, 257 μmol) in 2,2,2-trifluoroethanol (2 mL) was heated in a microwave at 150° C. for 6 h then cooled, concentrated and used in the next reaction without purification.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. customused in the next reaction without purification

Sources & evidence

ORD record
ord-45183f7897a143d5a6260560e025d265
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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