2-(2-Ethoxy-3-methoxyphenyl)ethanamine → (E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylamide hydrochloride

HRID 1362216Notes

Reaction equation

HRID 1362216 reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][N:10]2[CH2:15][C:14]3[CH:16]=[C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=O)[CH:18]=[N:19][C:13]=3[NH:12][C:11]2=[O:25])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl.[CH3:27][N:28]1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1.[CH2:45]([O:47][C:48]1[C:56]([O:57][CH3:58])=[CH:55][CH:54]=[CH:53][C:49]=1[CH2:50]CN)[CH3:46].CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[CH2:45]([O:47][C:48]1[C:56]([O:57][CH3:58])=[CH:55][CH:54]=[CH:53][C:49]=1[CH2:50][N:28]([CH3:27])[C:22](=[O:24])/[CH:21]=[CH:20]/[C:17]1[CH:18]=[N:19][C:13]2[NH:12][C:11](=[O:25])[N:10]([CH2:9][CH2:8][N:2]3[CH2:3][CH2:4][O:5][CH2:6][CH2:7]3)[CH2:15][C:14]=2[CH:16]=1)[CH3:46]

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 66967508(E)-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylic acid hydrochloride

Product 1

HCID 66966255(E)-N-(2-Ethoxy-3-methoxy-benzyl)-N-methyl-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylamide hydrochlorideYield 37%

Procedure

According to the procedure of Example 1, except substituting (E)-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-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 (155 mg, 37%) was prepared as a off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.15-10.13 (m, 2H), 8.40-8.35 (m, 1H), 8.00-7.92 (m, 1H), 7.54-7.42 (m, 1H), 7.25-7.20 (m, 1H), 7.13-6.68 (m, 2H), 6.66-6.61 (m, 1H), 5.11 (br s, 1H), 4.78-4.63 (m, 2H), 4.57-4.52 (m, 2H), 4.01-3.95 (m, 4H), 3.82-3.58 (m, 9H), 3.37-3.35 (m, 2H), 3.20-2.86 (m, 5H), 1.28-1.18 (m, 3H); MS (ESI) m/e 510 (M+H)+.

Sources & evidence

ORD record
ord-2523b0c96f004c1fae9ff93bc5bf5544
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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