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

HRID 1039038Notes

Reaction equation

HRID 1039038 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][NH:26]C(=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][NH2:26])=[CH:17]3)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67236341tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propylcarbamate

Product 1

HCID 672355912-(3-amino-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)propylcarbamate (3.0 g, 6.62 mmol), dichloromethane (33 mL), and 1M hydrochloric acid in diethyl ether (33 mL) and the resulting mixture stirred for 2 h. The resulting mixture was then concentrated in vacuo, the residue triturated with diethyl ether, and placed under high vacuum to yield 2-(3-amino-propyl)-1H-indole-5-carboxylic acid (3,4-dimethoxy-phenyl)-amide. MS (ES+) 354 (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=2.46 min.

Workup

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

Sources & evidence

ORD record
ord-9e1754906bbb48dba4b06ff08416ef46
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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