4-{4-[(4,5-dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester → 4,5-Dichloro-1-ethyl-1h-indole-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide hydrochloride salt

HRID 1645337Notes

Reaction equation

HRID 1645337 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24]([CH2:34][CH3:35])[C:25]4[C:30]([CH:31]=3)=[C:29]([Cl:32])[C:28]([Cl:33])=[CH:27][CH:26]=4)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.Cl.O1CCOCC1>[ClH:32].[N:11]1([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24]([CH2:34][CH3:35])[C:25]4[C:30]([CH:31]=3)=[C:29]([Cl:32])[C:28]([Cl:33])=[CH:27][CH:26]=4)=[O:22])=[CH:16][CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 593651314-{4-[(4,5-dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 667723914,5-Dichloro-1-ethyl-1h-indole-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide hydrochloride saltYield 212.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-{4-[(4,5-dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (750 mg, 1.45 mmol) in 15 mL of methylene chloride and 2 mL of 4M hydrogen chloride in dioxane was stirred at room temperature for 24 hr. The solvent was removed to afford 4,5-dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide hydrochloride salt (700 mg, 99% yield) as an off white solid. LCMS for C21H22Cl2N4O calcd. (m/e) 416, observed 417 (M+H).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-7f2ea9fa88c944269e0624e855b213dc
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

Loading…