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

HRID 1362192Notes

Reaction equation

HRID 1362192 reaction equation
[ClH:1].[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[CH2:19][CH2:18][CH2:17][CH2:16]1.Cl.[CH3:21][N:22]1[CH2:28][C:27]2[CH:29]=[C:30](/[CH:33]=[CH:34]/[C:35](O)=O)C=N[C:26]=2[NH:25][C:24](=O)[CH2:23]1.CNCC1N(C)C2C(C=1)=CC=CC=2.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[NH2:2][C:3]1[N:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([N:25]([CH3:26])[CH2:24][C:23]2[N:22]([CH3:21])[C:28]3[C:34]([CH:35]=2)=[CH:33][CH:30]=[CH:29][CH:27]=3)=[O:13])=[CH:5][C:4]=1[CH2:14][N:15]1[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 66967468(E)-3-(6-amino-5-pyrrolidin-1-ylmethyl-pyridin-3-yl)acrylic acid hydrochloride

Product 1

HCID 11743943(E)-3-(6-Amino-5-pyrrolidin-1-ylmethyl-pyridin-3-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide hydrochlorideYield 82%

Procedure

According to the procedure of Example 1, except substituting (E)-3-(6-amino-5-pyrrolidin-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 (223 mg, 82%) was prepared as a light, yellow powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.2 (br s, 1H), 8.35 (s, 1H), 8.21 (s, 1H), 7.52-7.39 (m, 3H), 7.24-7.01 (m, 4H), 6.41-6.16 (m, 1H), 5.05-4.85 (m, 2H), 4.29 (s, 2H), 3.74-3.68 (m, 3H), 3.10-3.00 (m, 6H), 2.10-1.82 (m, 5H); MS (ESI) m/e 404 (M+H)+.

Sources & evidence

ORD record
ord-27af847284864d1299bf8c8d7562bd90
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…