(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide → (E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-[N-(methylaminocarbonylmethyl)amino]pyridin-3-yl]acrylamide

HRID 18339Notes

Reaction equation

HRID 18339 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[CH2:12][N:13]([CH3:30])[C:14](=[O:29])/[CH:15]=[CH:16]/[C:17]1[CH:18]=[N:19][C:20]([NH:23][CH2:24][C:25]([O:27]C)=O)=[CH:21][CH:22]=1.COC([CH2:35][NH:36]C1N=CC(/C=C/C(N(C)CC2C3C(=CC=CC=3)NC=2C)=O)=CC=1)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[CH:8]=[C:7]2[CH2:12][N:13]([CH3:30])[C:14](=[O:29])/[CH:15]=[CH:16]/[C:17]1[CH:18]=[N:19][C:20]([NH:23][CH2:24][C:25]([NH:36][CH3:35])=[O:27])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 10363109(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamideHCID 11743240(E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methylacrylamide

Product 1

HCID 10002553(E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-N-methyl-3-[6-[N-(methylaminocarbonylmethyl)amino]pyridin-3-yl]acrylamideYield 94%

Procedure

According to the procedure of Example 21, except substituting (E)-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methylacrylamide (0.75 g, 1.8 mmole) for the (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide, the title compound (0.721 g, 94%) was prepared as a white solid: MS (ES) m/e 426.0 (M+H)+.

Sources & evidence

ORD record
ord-9492e528b80746d380d0ab45594b085b
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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