Dichloromethane → HCID 67229247, compound

HRID 1515854Notes

Reaction equation

HRID 1515854 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:17]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)[CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[NH:14][C:11]2=[N:12][CH:13]=1)(C)(C)C.[Cl:35]CCl>Cl>[ClH:35].[CH:19]1([CH2:18][CH:17]([C:15]2[NH:14][C:11]3=[N:12][CH:13]=[C:8]([NH2:7])[CH:9]=[C:10]3[CH:16]=2)[C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67229155{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester

Product 1

HCID 67229247HCID 67229247, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-carbamic acid tert-butyl ester (584 mg, 1.21 mmol) in dichloromethane (20 mL) was bubbled in dry hydrogen chloride gas for 30 min. The resulting mixture was stirred for 3 h at room temperature. The solvent was removed to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-ylamine hydrochloride salt (508 mg, 100%) which was used in the next step without purification: LC/MS m/e calcd for C21H25N3O2S [M+H]+ 384.52, observed 384.2.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-c8062bf8de254ee785938987aef3fa5d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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