2-Ethylhexanoyl chloride → Methyl 4-[5-(2-ethylhexanamido)indol-3-ylmethyl]-3methoxybenzoate

HRID 275119Notes

Reaction equation

HRID 275119 reaction equation
[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4](Cl)=[O:5])[CH3:2].[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33]>>[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 791032-Ethylhexanoyl chlorideHCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365894Methyl 4-[5-(2-ethylhexanamido)indol-3-ylmethyl]-3methoxybenzoateYield 76%

Procedure

Using a similar procedure to that described in Example 1, but starting from 2-ethylhexanoyl chloride and (A), there was obtained the title compound in 76% yield; partial NMR: 0.84(m,6H, 2×CH3), 1.24[m,6H, (CH2)3 ], 2.24(m,1H, CHCON), 10.78(d,1H, NH).

Sources & evidence

ORD record
ord-8d95d2aeea9943aab5f38a42403fbd5f
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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