Acrylic Acid → N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 1362052Notes

Reaction equation

HRID 1362052 reaction equation
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].Cl.[CH3:7][N:8]1[CH2:14][C:13]2[CH:15]=[C:16](/[CH:19]=[CH:20]/[C:21](O)=O)[CH:17]=[N:18][C:12]=2NC(=O)[CH2:9]1.CNCC1C2C(=CC=CC=2)N(C)C=1.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[CH3:17][N:18]([CH2:12][C:13]1[C:15]2[C:9](=[CH:21][CH:20]=[CH:19][CH:16]=2)[N:8]([CH3:7])[CH:14]=1)[C:1](=[O:5])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 6581Acrylic AcidHCID 109867781-Methyl-3-(methylaminomethyl)indoleHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

Product 1

HCID 22139011N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamideYield 58%

Procedure

According to the procedure of Example 1 (a), except substituting acrylic acid for the (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride, and substituting methyl-(1-methyl-1H-indol-3-ylmethyl)amine for the methyl-(1-propyl-napthalen-2-ylmethyl)amine, the title compound (1.51 g, 58%) was prepared as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.71-7.50 (s, 1H), 7.34-7.21 (m, 2H), 7.15-6.90 (m, 2H), 6.80-6.53 (m, 1H), 6.45-6.35 (s, 1H), 5.72-5.67 (m, 1H), 4.80-4.75 (m, 2H), 3.77 (s, 3H), 3.05-2.99 (m, 3H).

Sources & evidence

ORD record
ord-510121e92f484640b52ad7d77c17a246
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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