N-(5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-7-fluoro-1H-pyrrolo[3,2-c]pyridine-3-carbonyl}-pyridin-3-yl)-2-(3-cyclopropyl-pyrazol-1-yl)-acetamide → 2-(3-Cyclopropyl-pyrazol-1-yl)-N-{5-[7-fluoro-1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-pyrrolo[3,2-c]pyridine-3-carbonyl]-pyridin-3-yl}-acetamide

HRID 1752995Notes

Reaction equation

HRID 1752995 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([N:11]1[C:19]2[C:18]([F:20])=[CH:17][N:16]=[CH:15][C:14]=2[C:13]([C:21]([C:23]2[CH:24]=[C:25]([NH:29][C:30](=[O:40])[CH2:31][N:32]3[CH:36]=[CH:35][C:34]([CH:37]4[CH2:39][CH2:38]4)=[N:33]3)[CH:26]=[N:27][CH:28]=2)=[O:22])=[CH:12]1)([CH3:10])[CH3:9])(C)(C)C>C1COCC1>[CH:37]1([C:34]2[CH:35]=[CH:36][N:32]([CH2:31][C:30]([NH:29][C:25]3[CH:26]=[N:27][CH:28]=[C:23]([C:21]([C:13]4[C:14]5[CH:15]=[N:16][CH:17]=[C:18]([F:20])[C:19]=5[N:11]([C:8]([CH3:10])([CH3:9])[CH2:7][OH:6])[CH:12]=4)=[O:22])[CH:24]=3)=[O:40])[N:33]=2)[CH2:38][CH2:39]1

Participants

3

Reactant 1

HCID 90093921N-(5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-7-fluoro-1H-pyrrolo[3,2-c]pyridine-3-carbonyl}-pyridin-3-yl)-2-(3-cyclopropyl-pyrazol-1-yl)-acetamide

Product 1

HCID 736723422-(3-Cyclopropyl-pyrazol-1-yl)-N-{5-[7-fluoro-1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-pyrrolo[3,2-c]pyridine-3-carbonyl]-pyridin-3-yl}-acetamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-7-fluoro-1H-pyrrolo[3,2-c]pyridine-3-carbonyl}-pyridin-3-yl)-2-(3-cyclopropyl-pyrazol-1-yl)-acetamide (Preparation 6, 40 mg, 67 μmol) in THF (5 mL) 4M dioxane-HCl (1 mL) was added and stirred at room temperature for 18 hours. The reaction was evaporated in vacuo and triturated with pentane-ether to afford the title compound as an off white solid in 92% yield, 30 mg.

Workup

  1. customThe reaction was evaporated in vacuo
  2. customtriturated with pentane-ether

Sources & evidence

ORD record
ord-aa8c8e7b176745d8a0f08bc6fbe95a74
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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