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-(4-trifluoromethyl-phenyl)-acetamide → N-{5-[7-Fluoro-1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-pyrrolo[3,2-c]pyridine-3-carbonyl]-pyridin-3-yl}-2-(4-trifluoromethyl-phenyl)-acetamide

HRID 1753000Notes

Reaction equation

HRID 1753000 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:42])[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)[CH:26]=[N:27][CH:28]=2)=[O:22])=[CH:12]1)([CH3:10])[CH3:9])(C)(C)C>C1COCC1>[F:20][C:18]1[C:19]2[N:11]([C:8]([CH3:10])([CH3:9])[CH2:7][OH:6])[CH:12]=[C:13]([C:21]([C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:42])[CH2:31][C:32]4[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:41])[F:40])=[CH:36][CH:37]=4)[CH:26]=[N:27][CH:28]=3)=[O:22])[C:14]=2[CH:15]=[N:16][CH:17]=1

Participants

3

Reactant 1

HCID 90094115N-(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-(4-trifluoromethyl-phenyl)-acetamide

Product 1

HCID 73672463N-{5-[7-Fluoro-1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-pyrrolo[3,2-c]pyridine-3-carbonyl]-pyridin-3-yl}-2-(4-trifluoromethyl-phenyl)-acetamideYield 83%

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-(4-trifluoromethyl-phenyl)-acetamide (Preparation 1, 45 mg, 49 μmol) in THF (5 mL) 4M dioxane-HCl (0.5 mL) was added and stirred at room temperature for 2 hours. The reaction was evaporated in vacuo and triturated with pentane-ether to afford the title compound as a yellow solid in 83% yield, 30 mg.

Workup

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

Sources & evidence

ORD record
ord-1f039adc364b435680cea6817d689dee
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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