(1,7-Dimethyl-1H-indol-2-ylmethyl)methylamine → (E)-3-(6-Amino-5-morpholin-4-ylmethyl-pyridin-3-yl)-N-(1,7-dimethyl-1H-indol-2-ylmethyl)-N-methyl-acrylamide hydrochloride

HRID 1362185Notes

Reaction equation

HRID 1362185 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:11])[CH:4]=[C:3]1[CH2:12][NH:13][CH3:14].CNCC1C=CC2C(=CC=CC=2)C=1CCC.[ClH:31].[NH2:32][C:33]1[N:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([OH:43])=O)=[CH:35][C:34]=1[CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[ClH:31].[NH2:32][C:33]1[N:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([N:13]([CH2:12][C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][C:9]=3[CH3:11])[CH3:14])=[O:43])=[CH:35][C:34]=1[CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1

Participants

5

Reactant 4

HCID 59456930(1,7-Dimethyl-1H-indol-2-ylmethyl)methylamineHCID 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 66967363(E)-3-(6-amino-5-morpholin-4-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride

Product 1

HCID 10389964(E)-3-(6-Amino-5-morpholin-4-ylmethyl-pyridin-3-yl)-N-(1,7-dimethyl-1H-indol-2-ylmethyl)-N-methyl-acrylamide hydrochlorideYield 80%

Procedure

According to the procedure of Example 1, except substituting (1,7-dimethyl-1H-indol-2-ylmethyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(6-amino-5-morpholin-4-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, the title compound (0.31 g, 80%) was prepared as pale yellow powder: 1H NMR (300 MHz, DMSO-d6) δ 8.49 (s, 1H), 8.38-8.35 (m, 1H), 7.54-7.49 (m, 1H), 7.31-7.14 (m, 2H), 6.85-6.81 (m, 2H), 6.37-6.08 (m, 1H), 5.03-4.81 (m, 2H), 4.31 (br s, 2H), 3.96-3.72 (m, 7H), 3.42-2.99 (m, 10H), 2.72 (s, 3H); MS (ESI) m/e 434 (M+H)+.

Sources & evidence

ORD record
ord-b8c90fd9c3aa4c2897bee282e345ab86
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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