(S)-tert-butyl 2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoate → (S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acid

HRID 446949Notes

Reaction equation

HRID 446949 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][C@@H:16]([CH3:24])[C:17]([O:19]C(C)(C)C)=[O:18])=[O:14])=[CH:11][N:10]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1>FC(F)(F)CO>[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][C@@H:16]([CH3:24])[C:17]([OH:19])=[O:18])=[O:14])=[CH:11][N:10]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 67388507(S)-tert-butyl 2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoate

Product 1

HCID 67387896(S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A solution of (S)-tert-butyl 2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoate (265 mg, 0.58 mmol) in 2,2,2-trifluoroethanol (4 mL) was heated at 150° C. for 3 h under microwave assisted conditions. The solvent was removed under vacuum to give 230 mg (98%) of (S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acid as an oil.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7645b1e4253046bda7e840cac16fe5b2
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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