Cyclopentylacetyl chloride → Methyl 4-[5-(2-cyclopentylacetamido)indol-3-ylmethyl]-3-methoxybenzoate

HRID 1756412Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[O:22][CH3:23].[CH:24]1([CH2:29][C:30](Cl)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH:24]1([CH2:29][C:30]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Reactant 2

HCID 3485182Cyclopentylacetyl chloride

HCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365836Methyl 4-[5-(2-cyclopentylacetamido)indol-3-ylmethyl]-3-methoxybenzoate

Procedure

Starting from amino-ester (A), and using a similar procedure to that described in Example 4, except using cyclopentylacetyl chloride (see also Example 98), the title compound was obtained in quantitative yield as a foam; partial NMR (250 MHz, DMSO-d6): 1.2-1.8(3m,SH, cyclopentyl ring); 2.24(m,3H, CH2CONH and --CHCH2); 3.83(s,3H, OMe); 3.93(s,3H, OMe); 3.99(br s,2H, CH2Ar); 9.57(br s,1H, NHCO); 10.79(br d, 1H, --NH--).

Sources & evidence

ORD record: ord-42b00a60266d4cd6838ef44faf429dba
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05440035

Reaction notes

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