4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 68678839, compound

HRID 1989070Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[C:8]2[CH:13]=[N:12][C:11](S(C)(=O)=O)=[N:10][C:9]=2[N:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][CH2:24][CH2:23]3)[CH:19]=1)=[O:5])[CH3:2].[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[CH2:33][CH2:32]1>CC(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[C:8]2[CH:13]=[N:12][C:11]([NH:44][C:41]3[CH:40]=[CH:39][C:38]([CH2:37][N:34]4[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]4)=[CH:43][CH:42]=3)=[N:10][C:9]=2[N:18]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[CH2:25][CH2:24][CH2:23]3)[CH:19]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

8-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.098 g, 0.24 mmol) and 4-(4-methyl-piperazin-1-ylmethyl)-phenylamine (0.049 g, 0.24 mmol) were combined in i-PrOH (2 mL) and heated to 90° C. After 3 h, the reaction mixture was concentrated and purified by preparative HPLC (30 mL/min 5-100% MeCN/H2O gradient over 10 min) and lyophilized to provide 20 mg of 8-Indan-5-yl-2-[4-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.36 (s, 1H), 8.54 (s, 1H), 7.43 (d, 2H, J=7.9 Hz), 7.29 (m, 2H), 7.18 (dd, 2H, J=2.0 Hz, J=7.9 Hz), 7.03-7.05 (m, 1H), 4.38 (q, 2H, J=7.1 Hz), 3.44 (s, 2H), 3.08 (t, 2H, J=7.4 Hz), 3.01 (t, 2H, J=7.5 Hz), 2.52 (br s, 8H), 2.36 (s, 3H), 2.19-2.29 (m, 2H), 1.39 (t, 3H, J=7.1 Hz).

Workup

concentrationthe reaction mixture was concentrated
custompurified by preparative HPLC (30 mL/min 5-100% MeCN/H2O gradient over 10 min)

Sources & evidence

ORD record: ord-f6c00fb294ce4370a7ef1f3ef686e21d
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

Loading…