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

HRID 1297464Notes

Reaction equation

HRID 1297464 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:26])=[CH:21][CH:22]=1.COC(CNC1N=CC(/C=C/C(N(C)CC2C3C(=CC=CC=3)NC=2C)=O)=CC=1)=O>>[C:25]([CH2:24][NH:23][C:20]1[N:19]=[CH:18][C:17](/[CH:16]=[CH:15]/[C:14]([N:13]([CH2:12][C:7]2[C:6]3[C:10](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=3)[N:9]([CH3:11])[CH:8]=2)[CH3:30])=[O:29])=[CH:22][CH:21]=1)([OH:27])=[O:26]

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 10001757(E)-3-[6-[N-(carboxymethyl)amino]pyridin-3-yl]-N-(7-chloro-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamideYield 100.4%

Procedure

According to the procedure of Example 20, 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 (0.746 g, 100%) was prepared as a white solid: MS (ES) m/e 413.2 (M+H)+.

Sources & evidence

ORD record
ord-d53b489188b54f089beae35933f38f79
Source dataset
uspto-grants-2007_07
Patent number
US07250424B2

Reaction notes

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