2-(2-Ethoxy-3-methoxyphenyl)ethanamine → (E)-3-[6-Amino-5-(4-methyl-piperazin-1-ylmethyl)pyridin-3-yl]-N-(2-ethoxy-3-methoxy-benzyl)-N-methyl-acrylamide hydrochloride

HRID 1362200Notes

Reaction equation

HRID 1362200 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[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.Cl.[CH3:23][N:24]1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1.[CH2:41]([O:43][C:44]1[C:52]([O:53][CH3:54])=[CH:51][CH:50]=[CH:49][C:45]=1[CH2:46]CN)[CH3:42].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:24]([CH2:46][C:45]2[CH:49]=[CH:50][CH:51]=[C:52]([O:53][CH3:54])[C:44]=2[O:43][CH2:41][CH3:42])[CH3:23])=[O:13])=[CH:5][C:4]=1[CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]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 66967158(E)-3-[6-amino-5-(4-methyl-piperazin-1-ylmethyl)pyridin-3-yl]acrylic acid hydrochloride

Product 1

HCID 10413258(E)-3-[6-Amino-5-(4-methyl-piperazin-1-ylmethyl)pyridin-3-yl]-N-(2-ethoxy-3-methoxy-benzyl)-N-methyl-acrylamide hydrochlorideYield 25%

Procedure

According to the procedure of Example 1, except substituting (E)-3-[6-amino-5-(4-methyl-piperazin-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 (2-ethoxy-3-methoxy-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (177 mg, 25%) was prepared as a pale, yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.4 (s, 1H), 8.28-8.19 (m, 2H), 7.73 (s, 1H), 7.47 (d, J=15.3 Hz, 1H), 7.21 (dd, J=14.9, 5.4 Hz, 1H), 7.05-6.94 (m, 2H), 6.64 (dd, J=7.2, 7.2 Hz, 1H), 4.78-4.63 (m, 2H), 4.03-3.93 (m, 2H), 3.79 (s, 3H), 3.55-3.33 (m, 7H), 3.09-2.85 (m, 7H), 2.74 (s, 3H), 1.31-1.25 (m, 3H); MS (ESI) m/e 454 (M+H)+.

Sources & evidence

ORD record
ord-7ca27b5663b6469ab59569e46c3a482d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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