1-Methylpiperazine → (E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-{3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl}acrylamide hydrochloride

HRID 1711909Notes

Reaction equation

HRID 1711909 reaction equation
[CH3:1][N:2]([CH2:22][C:23]1[N:24]([CH3:32])[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:3](/[CH:5]=[CH:6]/[C:7]1[CH:21]=[N:20][C:10]2[NH:11][C:12](=[O:19])[N:13]([CH2:15][C:16](O)=[O:17])[CH2:14][C:9]=2[CH:8]=1)=[O:4].[ClH:33].C[N:35]1[CH2:41][C:40]2C=C(/C=C/C(O)=O)C=N[C:39]=2[NH:38][C:37](=O)[CH2:36]1.CN1CCNCC1.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:33].[CH3:1][N:2]([CH2:22][C:23]1[N:24]([CH3:32])[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:3](=[O:4])/[CH:5]=[CH:6]/[C:7]1[CH:21]=[N:20][C:10]2[NH:11][C:12](=[O:19])[N:13]([CH2:15][C:16]([N:35]3[CH2:36][CH2:37][N:38]([CH3:39])[CH2:40][CH2:41]3)=[O:17])[CH2:14][C:9]=2[CH:8]=1

Participants

5

Reactant 4

HCID 531671-MethylpiperazineHCID 9980301(E)-(6-{2-[Methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acidHCID 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 hydrochloride

Product 1

HCID 66967406(E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-{3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl}acrylamide hydrochlorideYield 43%

Procedure

According to the procedure of Example 1, except substituting (E)-(6-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid 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 1-methylpiperazine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (173 mg, 43%) was prepared as a off-white solid: 1H NMR (300 MHz, DMSO-d6) □ 10.78 (br s, 1H), 10.07-10.03 (m, 1H), 8.41-8.37 (m, 1H), 7.98-7.90 (m, 1H), 7.57-7.39 (m, 3H), 7.25-6.99 (m, 3H), 6.42-6.17 (m, 1H), 5.04-4.85 (m, 2H), 4.46-4.03 (m, 5H), 3.72-3.68 (m, 3H), 3.44-3.41 (m, 3H), 3.11-2.91 (m, 7H), 2.78 (s, 3H); MS (ESI) m/e 516 (M+H)+.

Sources & evidence

ORD record
ord-5c1cececdf9d4685aac6719dd89393d2
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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