2-(2-Ethoxy-3-methoxyphenyl)ethanamine → (E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl}acrylamide hydrochloride

HRID 1362179Notes

Reaction equation

HRID 1362179 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].[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:39](=[O:58])[CH2:40][N:41]2[CH2:47][C:46]3[CH:48]=[C:49](/[CH:52]=[CH:53]/[C:54]([OH:56])=O)[CH:50]=[N:51][C:45]=3[NH:44][C:43](=[O:57])[CH2:42]2)[CH2:35][CH2:34]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[ClH:31].[CH2:1]([O:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][N:16]([CH3:15])[C:54](=[O:56])/[CH:53]=[CH:52]/[C:49]1[CH:50]=[N:51][C:45]2[NH:44][C:43](=[O:57])[CH2:42][N:41]([CH2:40][C:39]([N:36]3[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]3)=[O:58])[CH2:47][C:46]=2[CH:48]=1)[CH3:2]

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 66967110(E)-3-{4-[2-(4-Methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl}acrylic acid hydrochloride

Product 1

HCID 10438325(E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl}acrylamide hydrochlorideYield 47%

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-{4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-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 (82 mg, 47%) was prepared as an off-white powder: 1H NMR (300 MHz, DMSO-d6) δ 10.97 (br s, 1H), 10.67 (br s, 1H), 8.64-8.60 (m, 1H), 8.23-8.14 (m, 1H), 7.58-7.52 (m, 1H), 7.39-7.33 (m, 1H), 7.07-6.94 (m, 2H), 6.69-6.63 (m, 1H), 4.80-4.64 (m, 2H), 4.42-4.38 (m, 1H), 4.09-3.93 (m, 3H), 3.79 (s, 3H), 3.68 (br s, 2H), 3.47-3.37 (m, 8H), 3.11-2.97 (m, 5H), 2.75 (br s, 3H), 1.31-1.24 (m, 3H); MS (ESI) m/e 551 (M+H)+.

Sources & evidence

ORD record
ord-01a8732bdc1d48eca844c28f4366671b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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