2-(2-Ethoxy-3-methoxyphenyl)ethanamine → (E)-3-(6-Amino-5-morpholin-4-ylmethyl-Pyridin-3-yl)-N-(2-ethoxy-3-methoxy-benzyl)-N-methyl-acrylamide hydrochloride

HRID 1362186Notes

Reaction equation

HRID 1362186 reaction equation
[CH2:1]([O:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6]CN)[CH3:2].[CH3:15][NH:16]CC1C=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:16]([CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:4]=2[O:3][CH2:1][CH3:2])[CH3:15])=[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 47154242-(2-Ethoxy-3-methoxyphenyl)ethanamineHCID 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 10344943(E)-3-(6-Amino-5-morpholin-4-ylmethyl-Pyridin-3-yl)-N-(2-ethoxy-3-methoxy-benzyl)-N-methyl-acrylamide hydrochlorideYield 70%

Procedure

According to the procedure of Example 1, except substituting (2-ethoxy-3-methoxy-benzyl)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 (0.27 g, 70%) was prepared as pale yellow powder: 1H NMR (300 MHz, DMSO-d6) δ 8.83-8.65 (m, 1H), 8.40 (s, 1H), 7.52-7.45 (m, 1H), 7.29-7.24 (m, 1H), 7.04-6.96 (m, 2H), 6.65-6.64 (m, 1H), 4.80-4.64 (m, 2H), 4.35 (br s, 2H), 4.02-3.79 (m, 10H), 3.39-2.83 (m, 8H), 1.31-1.25 (m, 3H); MS (ESI) m/e 441 (M+H)+.

Sources & evidence

ORD record
ord-e1deb92fdcd04a2cafe859b2196dcbe7
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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