Hydrochloric Acid → 2-(3-methylamino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide

HRID 1039042Notes

Reaction equation

HRID 1039042 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([CH2:23][CH2:24][CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)=[CH:17]3)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClCCl.Cl>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([CH2:23][CH2:24][CH2:25][NH:26][CH3:27])=[CH:17]3)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67235276tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propyl(methyl)carbamate

Product 1

HCID 672359102-(3-methylamino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 250 round bottom flask was charged with tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propyl(methyl)carbamate (2.75 g, 5.88 mmol), dichloromethane (32 mL), and 1M hydrochloric acid in diethyl ether (32 mL) and the resulting mixture stirred for 2.5 h. The resulting mixture was then concentrated in vacuo, the residue triturated with diethyl ether, and placed under high vacuum to yield 2-(3-methylamino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide. MS (ES+) 368 (M+1); HPLC: Kromasil C18 column (50×2 mm; 3.5μ), gradient 10-90% (MeCN+0.16% TFA) in (water+0.2% TFA) over 4 min, tR=2.72 min.

Workup

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-84cf068e6ff545809b23f6844dc9a4d7
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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