Hydrochloric Acid → HCID 117899671, compound

HRID 522301Notes

Reaction equation

HRID 522301 reaction equation
[ClH:1].[Si]([O:9][CH2:10][CH2:11][N:12]1[C:16]2[N:17]=[C:18]([C:47]#[N:48])[N:19]=[C:20]([C:21]3[CH:42]=[CH:41][C:24]([O:25][CH2:26][CH2:27][CH:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[C:23]([C:43]([F:46])([F:45])[F:44])[CH:22]=3)[C:15]=2[CH:14]=[CH:13]1)(C(C)(C)C)(C)C>O1CCOCC1>[ClH:1].[OH:9][CH2:10][CH2:11][N:12]1[C:16]2[N:17]=[C:18]([C:47]#[N:48])[N:19]=[C:20]([C:21]3[CH:42]=[CH:41][C:24]([O:25][CH2:26][CH2:27][CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)=[C:23]([C:43]([F:46])([F:45])[F:44])[CH:22]=3)[C:15]=2[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735525HCID 131735525, compound

Product 1

HCID 117899671HCID 117899671, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4 M solution of hydrogen chloride in dioxane (1 ml) was added to a solution of tert-butyl 4-(2-{4-[7-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate (150 mg) in dioxane (1 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour. After the reaction mixture was concentrated under reduced pressure, the precipitate was washed with diisopropyl ether, and collected by filtration, whereby 7-(2-hydroxyethyl)-4-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride (110 mg) was obtained as a pale yellow solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. washthe precipitate was washed with diisopropyl ether
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3b5b9edb756543a3ba4b65e4c702089f
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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