Hydrochloric Acid → 5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid {2-[4-(2-amino-2-methyl-propionyl)-piperazin-1-yl]-ethyl}-amide

HRID 1359872Notes

Reaction equation

HRID 1359872 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:53])([CH3:52])[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][NH:19][C:20]([C:22]2[C:26]([CH3:27])=[C:25](/[CH:28]=[C:29]3\[C:30](=[O:50])[NH:31][C:32]4[C:37]\3=[CH:36][C:35]([S:38]([CH2:41][C:42]3[C:47]([Cl:48])=[CH:46][CH:45]=[CH:44][C:43]=3[Cl:49])(=[O:40])=[O:39])=[CH:34][CH:33]=4)[NH:24][C:23]=2[CH3:51])=[O:21])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.Cl>C(Cl)Cl.C(OCC)(=O)C>[NH2:7][C:8]([CH3:53])([CH3:52])[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][NH:19][C:20]([C:22]2[C:26]([CH3:27])=[C:25](/[CH:28]=[C:29]3\[C:30](=[O:50])[NH:31][C:32]4[C:37]\3=[CH:36][C:35]([S:38]([CH2:41][C:42]3[C:43]([Cl:49])=[CH:44][CH:45]=[CH:46][C:47]=3[Cl:48])(=[O:40])=[O:39])=[CH:34][CH:33]=4)[NH:24][C:23]=2[CH3:51])=[O:21])[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69994415(2-{4-[2-({5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-ethyl]-piperazin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 590775015-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid {2-[4-(2-amino-2-methyl-propionyl)-piperazin-1-yl]-ethyl}-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of (2-{4-[2-({5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-ethyl]-piperazin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (from the above reaction) in DCM (3 mL) was added 6N HCl in ethyl acetate. The mixture was stirred at 40° C. for 3 hours. The reaction was concentrated, basified to pH 7-8 with 2N NaOH, extracted with DCM and concentrated. The residue was purified on a silica gel column to give 40 mg the titled compound as a red solid.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with DCM
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-95aa8973de3e44328fbfcdaf9d601c79
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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