Ethylamine → HCID 16059141, compound

HRID 1989083Notes

Reaction equation

HRID 1989083 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:40])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH2:36][CH2:35][CH2:34]3)[CH:30]=1)=O)C.[CH2:41]([NH2:43])[CH3:42]>CO>[CH2:41]([NH:43][C:4]([C:6]1[C:7](=[O:40])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH2:36][CH2:35][CH2:34]3)[CH:30]=1)=[O:3])[CH3:42]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 68678839HCID 68678839, compound

Product 1

HCID 16059141HCID 16059141, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

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 (9.2 mg, 0.017 mmol) was dissolved in MeOH (1 mL) and ethylamine (1 mL of 1.0 M solution in THF, 1.0 mmol) was added and the reaction mixture was heated at 80° C. After 16 h, the solution was cooled to rt and purified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min) and lyophilized to provide 5.2 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 ethylamide. 1H NMR TFA salt (400 MHz, CDCl3) δ (ppm): 9.38 (br s, 1H), 9.37 (s, 1H), 8.84 (s, 1H), 7.58-7.60 (m, 1H), 7.40-7.47 (m, 2H), 7.16 (dd, 2H, J=2.0 Hz, J=7.9 Hz), 7.05 (br s, 2H), 3.43-3.55 (m, 4H), 3.07 (t, 2H, J=7.3 Hz), 2.99 (t, 2H, J=7.4 Hz), 2.53 (br s, 8H), 2.36 (s, 3H), 2.18-2.27 (m, 2H), 1.15-1.39 (m, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C31H35N7O2: 537.29, Found: 538.3 (M+H).

Workup

  1. temperaturethe solution was cooled to rt
  2. custompurified by preparative HPLC (C-18 column, 32 mL/min 5-100% MeCN/H2O gradient over 15 min)

Sources & evidence

ORD record
ord-ff73badd9bd849409342554ed42b569f
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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