Hydrochloric Acid → 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(pyrrolidinocarbonyl)ethyl]indol1-ylmethyl]-3-methoxybenzoic acid

HRID 1198967Notes

Reaction equation

HRID 1198967 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:31][CH2:32][C:33](OC)=[O:34])=[CH:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CN(C)C1C=CN=CC=1.N1CCCC1.O>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:31][CH2:32][C:33]([N:16]4[CH2:17][CH2:13][CH2:14][CH2:15]4)=[O:34])=[CH:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 150137794-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid

Product 1

HCID 150137824-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(pyrrolidinocarbonyl)ethyl]indol1-ylmethyl]-3-methoxybenzoic acidYield 169.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 31268PyrrolidineSolvent

Procedure

A solution of 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.84 g) (prepared as described in Example 1, parts (a) through (i)) and 4-(dimethylamino)pyridine (0.21 g) in pyrrolidine (5 ml) was heated at 80° for 48 hours under a nitrogen atmosphere. The reaction was diluted with water and acidified with 10% (v/v) hydrochloric acid. The resultant precipitate was collected by filtration and washed with water to give 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(pyrrolidinocarbonyl)ethyl]indol1-ylmethyl]-3-methoxybenzoic acid as a white powder (0.77 g, 85%): partial NMR (80 MHz, DMSO-d6 : 1.1-2.0 (m, 12H), 2.1(m, 1H, NHCH2CH), 3.9(s, 3H, OCH3), 6.7(d, 1H, Ar), 7.3(s, 1H, H2 -indole), 8.3(t,1H, NH).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-e0d19e05ab7a4c968e973f7f8e51dac3
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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