Hydrochloric Acid → N-[5-({7-[(1S)-2-hydroxy-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]-2-[3-(trifluoromethyl)phenyl]acetamide

HRID 82088Notes

Reaction equation

HRID 82088 reaction equation
Cl.C([Si](C)(C)[O:7][CH2:8][C@@H:9]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[CH:19][C:14]=2[C:13]([C:20]([C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:41])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[CH:25]=[N:26][CH:27]=2)=[O:21])=[CH:12]1)[CH3:10])(C)(C)C>O1CCOCC1.C1COCC1>[OH:7][CH2:8][C@@H:9]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[CH:19][C:14]=2[C:13]([C:20]([C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:41])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:40])[F:38])[CH:32]=3)[CH:25]=[N:26][CH:27]=2)=[O:21])=[CH:12]1)[CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70817237HCID 70817237, compound

Product 1

HCID 70817662N-[5-({7-[(1S)-2-hydroxy-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]-2-[3-(trifluoromethyl)phenyl]acetamideYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

10% Hydrochloric acid in 1,4-dioxane (0.2 mL) was added to N-(5-{7-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(3-trifluoromethyl-phenyl)-acetamide (Preparation 105, 59 mg, 0.098 mmol) in THF (2 mL) and the mixture was stirred at room temperature for 18 hours. The mixture was evaporated in vacuo and triturated with ether-pentane to afford the title compound as an off white solid in 86% yield, 41 mg.

Workup

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

Sources & evidence

ORD record
ord-a29cadabf95349e5af50dceceee746a8
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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