Hydrochloric Acid → HCID 117899593, compound

HRID 522297Notes

Reaction equation

HRID 522297 reaction equation
[ClH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]4[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][O:32][CH3:33])[C:21]=4[N:22]=[C:23]([C:25]#[N:26])[N:24]=3)=[CH:15][C:14]=2[C:34]([F:37])([F:36])[F:35])[CH2:6][CH2:5]1)[CH3:3]>CCOC(C)=O.C(Cl)Cl>[ClH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]4[CH:29]=[CH:28][N:27]([CH2:30][CH2:31][O:32][CH3:33])[C:21]=4[N:22]=[C:23]([C:25]#[N:26])[N:24]=3)=[CH:15][C:14]=2[C:34]([F:36])([F:37])[F:35])[CH2:6][CH2:5]1)[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90065727HCID 90065727, compound

Product 1

HCID 117899593HCID 117899593, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 4 M solution of hydrogen chloride in EtOAc (0.12 mL) was added to a solution of 4-{4-[2-(1-ethylpiperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (80 mg) in CH2Cl2 (1.5 mL) at room temperature, and the mixture was stirred at the same temperature for 0.5 hours. The reaction mixture was concentrated under reduced pressure, and diisopropyl ether was added to the residue. The precipitate was washed with diisopropyl ether, and collected by filtration, whereby 4-{4-[2-(1-ethylpiperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride (50 mg) was obtained as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and diisopropyl ether
  2. additionwas added to the residue
  3. washThe precipitate was washed with diisopropyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7f9795351e3840ee8c518f4a4e44e90e
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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