4-(4-Methylpiperazin-1-yl)aniline → HCID 16059408, compound

HRID 1989021Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[C:8]2[CH:13]=[N:12][C:11](S(C)(=O)=O)=[N:10][C:9]=2[N:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:19]=1)=[O:5])[CH3:2].[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>CC(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[C:8]2[CH:13]=[N:12][C:11]([NH:40][C:37]3[CH:36]=[CH:35][C:34]([N:31]4[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]4)=[CH:39][CH:38]=3)=[N:10][C:9]=2[N:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:19]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

8-Cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (20 mg, 0.051 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (10 mg, 0.051 mmol) were combined in i-PrOH (2 mL) and heated to 80° C. After 14 h, the solution was concentrated and purified by preparative HPLC (30 mL/min 0-100% H2O/MeCN gradient over 10 min) to provide 7.2 mg (29%) of 8-cyclohexyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3:) δ ppm 9.32 (s, 1H), 8.31 (s, 1H), 7.57 (d, 2H, J=9.0 Hz), 6.96 (d, 1H, J=8.9 Hz), 4.40 (q, 2H, J=7.1 Hz), 3.25-3.46 (m, 8H), 2.82-2.84 (m, 3H), 1.49-2.0 (m, 8H), 1.41 (t, 3H, J=7.1 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C27H34N6O3: 490.27, found: (M+H) 491.3.

Workup

concentrationthe solution was concentrated
custompurified by preparative HPLC (30 mL/min 0-100% H2O/MeCN gradient over 10 min)

Sources & evidence

ORD record: ord-6d7ac272ca0a49ec8df9591b1fff505c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

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