methyl((1-methyl-1H-indol-2-yl)methyl)amine → (E)-3-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide

HRID 1362191Notes

Reaction equation

HRID 1362191 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)=[CH:5][C:4]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.Cl.[CH3:22][N:23]1[CH2:29][C:28]2[CH:30]=[C:31](/[CH:34]=[CH:35]/[C:36](O)=O)C=N[C:27]=2[NH:26][C:25](=O)[CH2:24]1.CNCC1N(C)C2C(C=1)=CC=CC=2.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([N:26]([CH3:27])[CH2:25][C:24]2[N:23]([CH3:22])[C:29]3[C:35]([CH:36]=2)=[CH:34][CH:31]=[CH:30][CH:28]=3)=[O:13])=[CH:5][C:4]=1[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 4

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 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 hydrochlorideHCID 66966962(E)-3-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride

Product 1

HCID 10409739(E)-3-(6-Amino-5-piperidin-1-ylmethyl-pyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamideYield 54%

Procedure

According to the procedure of Example 1 (a), except substituting (E)-3-(6-amino-5-piperidin-1-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride 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-2-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (294 mg, 54%) was prepared as an off-white powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.12 (s, 1H), 7.78-7.68 (m, 1H), 7.49-7.38 (m, 3H), 7.14-6.97 (m, 3H), 6.63 (s, 2H), 6.41-6.18 (m, 1H), 5.02-4.83 (m, 2H), 3.72-3.67 (m, 3H), 3.39-3.34 (m, 3H), 3.09-2.96 (m, 3H), 2.29 (br s, 3H), 1.49-1.40 (m, 6H); MS (ESI) m/e 418 (M+H)+.

Sources & evidence

ORD record
ord-39c138f16b6f4bc696c4f7553ac7f458
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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