1-Methyl-3-(methylaminomethyl)indole → HCID 66967302, compound

HRID 1362187Notes

Reaction equation

HRID 1362187 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[CH:5]=1.CNCC1C=CC2C(=CC=CC=2)C=1CCC.[O:30]=[C:31]1[NH:36][C:35]2[N:37]=[CH:38][C:39](/[CH:41]=[CH:42]/[C:43]([OH:45])=O)=[CH:40][C:34]=2[C:33](=[O:46])[NH:32]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[O:30]=[C:31]1[NH:36][C:35]2[N:37]=[CH:38][C:39](/[CH:41]=[CH:42]/[C:43]([N:2]([CH3:1])[CH2:3][C:4]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]([CH3:13])[CH:5]=3)=[O:45])=[CH:40][C:34]=2[C:33](=[O:46])[NH:32]1

Participants

5

Reactant 4

HCID 109867781-Methyl-3-(methylaminomethyl)indoleHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 59456972HCID 59456972, compoundHCID 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 66967302HCID 66967302, compoundYield 34%

Procedure

According to the procedure of Example 1 (a), except substituting methyl-(1-methyl-1H-indol-3-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)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, the title compound (0.16 g, 34%) was prepared as a tan solid and as a mixture of amide rotamers; 1H NMR (300 MHz, DMSO-d6) δ 11.84 (s, 1H), 11.53 (s, 1H), 8.91 (s, 1H), 8.73-8.66 (m, 1H), 7.78-7.30 (m, 5H), 7.17-7.12 (m, 1H), 7.03-6.98 (m, 1H), 4.96-4.73 (m, 2H), 3.76 (s, 3H), 3.07-2.90 (m, 3H); MS (ESI) m/e 390 (M+H)+.

Sources & evidence

ORD record
ord-d96ab4ba11b0495f8a7b44b52ebce160
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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