Ethylamine → HCID 58832267, compound

HRID 1989082Notes

Reaction equation

HRID 1989082 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:37])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:28]([CH:30]2[CH2:35][CH:34]3[CH2:36][CH:31]2[CH2:32][CH2:33]3)[CH:29]=1)=O)C.[CH2:38]([NH2:40])[CH3:39]>CO>[CH2:38]([NH:40][C:4]([C:6]1[C:7](=[O:37])[C:8]2[CH:13]=[N:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[N:10][C:9]=2[N:28]([CH:30]2[CH2:35][CH:34]3[CH2:36][CH:31]2[CH2:32][CH2:33]3)[CH:29]=1)=[O:3])[CH3:39]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 68676848HCID 68676848, compound

Product 1

HCID 58832267HCID 58832267, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

8-Bicyclo[2.2.1]hept-2-yl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (5.7 mg, 0.11 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 3.7 of 8-bicyclo[2.2.1]hept-2-yl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethylamide. 1H NMR (TFA salt) (400 MHz, CDCl3) δ (ppm): 9.62 (s, 1H), 9.26 (s, 1H), 8.90 (s, 1H), 7.54 (d, 2H, J=8.8 Hz), 6.89 (d, 2H, J=8.9 Hz), 4.85-4.88 (m, 1H), 3.26-3.64 (m, 9H), 2.91-2.94 (m, 2H), 2.82 (s, 3H), 2.55 (s, 1H), 2.44 (s, 1H), 2.03 (br s, 8H), 1.59-1.61 (m, 4H), 1.35-1.41 (m, 2H), 1.19 (t, 1H, J=7.3 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. for C28H35N7O2: 501.29, Found: 502.3 (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-f126a89cdcf84726815c5866d72a9837
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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