Hydrochloric Acid → N-(3-Aminopropyl)-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

HRID 1695103Notes

Reaction equation

HRID 1695103 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:18]([CH3:19])=[C:17](/[CH:20]=[C:21]2\[C:22](=[O:31])[NH:23][C:24]3[C:29]\2=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[NH:16][C:15]=1[CH3:32])=[O:13])(C)(C)C.Cl>CO.O1CCOCC1>[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:18]([CH3:19])=[C:17](/[CH:20]=[C:21]2\[C:22](=[O:31])[NH:23][C:24]3[C:29]\2=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[NH:16][C:15]=1[CH3:32])=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67274068HCID 67274068, compound

Product 1

HCID 16722152N-(3-Aminopropyl)-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamideYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

[3-({5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-propyl]-carbamic acid tert-butyl ester was suspended in methanol. 2 ml of HCl (4N) in dioxane was added and the reaction stirred at room temperature overnight. The solvent was removed to yield the desired compound (0.098 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ 13.8 (s, 1H); 11.00 (s, 1H); 7.90-7.70 (m, 5H); 6.9 (m, 2H); 3.30 (q, 2H); 2.80 (q, 2H); 2.50 (dd, 6H) 1.80 (m, 2H). LCMS: inconclusive due to fluorescence.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-a76f7acf9a0848028fde7b9b74be7da3
Source dataset
uspto-grants-2012_04
Patent number
US08163511B2

Reaction notes

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