Hydrochloric Acid → HCID 19870609, compound

HRID 330148Notes

Reaction equation

HRID 330148 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH2:32][CH2:33][C:34](OC)=[O:35])=[CH:16][N:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C)C1C=CN=CC=1.O>[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([C:15]([CH2:32][CH2:33][C:34]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[O:35])=[CH:16][N:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:13][CH:12]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 19870621HCID 19870621, compound

Product 1

HCID 19870609HCID 19870609, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A solution of 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.40 g) and 4-dimethylaminopyridine (0.10 g) in morpholine (3 ml) was heated at 80° for 52 hr. The reaction was diluted with water and acidified to pH 1 with 10% (v/v) hydrochloric acid to form a precipitate which was collected by filtration to give 4-[6-(cyclopentylmethylcarbamoyl)methyl-3-(2-morpholinocarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.34 g, 75%) as an ivory solid; partial NMR (250 MHz, CDCl3): 2.72(t, 2H, COCH2), 3.35-3.60(8H, morpholino), 3.66(s, 2H, COCH2Ar), 3.95(s, 3H, OCH3), 5.29(s, 2H, NCH2Ar). (It will be recognized that this compound is also an example of the invention.)

Workup

  1. customto form a precipitate which
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b0933be319a1432480718104e7e1e68a
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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