4-(4-Methylpiperazin-1-yl)aniline → 2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-5-oxo-8-phenyl-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 1989014Notes

Reaction equation

HRID 1989014 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CS([C:19]1[N:20]=[CH:21][C:22]2[C:28](=[O:29])[C:27]([C:30]#[N:31])=[CH:26][N:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:23]=2[N:24]=1)(=O)=O>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:19]3[N:20]=[CH:21][C:22]4[C:28](=[O:29])[C:27]([C:30]#[N:31])=[CH:26][N:25]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:23]=4[N:24]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 68678798HCID 68678798, compound

Product 1

HCID 686772462-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-5-oxo-8-phenyl-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonitrile

Procedure

Using the procedure outlined in Example 1(G) the title compound was prepared from 4-(4-methyl-piperazin-1-yl)-phenylamine (32 mg, 0.16 mmol) and 2-methanesulfonyl-5-oxo-8-phenyl-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonitrile (Example 13 (D) above, 50 mg, 0.15 mmol). The product was obtained as a yellow solid (17.1 mg). 1H NMR (300 MHz, CDCl3) δ (ppm): 9.34 (s, 1H), 8.55 (br, 1H), 7.61 (m, 3H), 7.41 (d, 2H), 7.24 (m, 2H), 6.55 (d, 2H), 3.00 (m, 4H), 2.55 (m, 4H), 2.35 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H23N7O: 438.20 (M+H), Found: 438.5.

Sources & evidence

ORD record
ord-32829baafe9642b7a0023974b4675131
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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