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Ethylamine → 8-Indan-5-yl-2-[4-(2-morpholin-4-yl-ethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

HRID 1989036
Notes
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Reaction equation

HRID 1989036 reaction equation
C(O[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][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]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:5])C.[CH2:41]([NH2:43])[CH3:42]>CO.C1COCC1>[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:16]=[CH:17][C:18]([CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:20]=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:5])[CH3:42]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6341EthylamineHCID 25223480HCID 25223480, compound

Product 1

HCID 160595368-Indan-5-yl-2-[4-(2-morpholin-4-yl-ethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl amideYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-indan-5-yl-2-[4-(2-morpholin-4-yl-ethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 27 (b), 20 mg, 0.037 mmol) in 1 mL methanol was added a solution of ethylamine in THF (2N, 2 mL). The mixture was stirred at 80° C. for 16 hours. The solvent was removed by vacuum to leave a yellow solid (12.7 mg, 64%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.60 (br, 1H), 9.29 (s, 1H), 8.78 (s, 1H), 7.75 (s, 1H), 7.60 (br, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.20 (m, 2H), 7.12 (d, J=7.6 Hz, 1H), 6.87 (br, 2H), 3.69 (br, 4H), 3.42(q, J=7.1 Hz, 2H), 3.01 (t, J=7.3 Hz, 2H), 2.93 (t, J=7.4 Hz, 2H), 2.65 (br, 2H), 2.49 (br, 6H), 2.17 (m, 2H). 1.08 (t, 7.1 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C31H34N6O3: 539.27 (M+H), Found 539.0.

Workup

  1. customThe solvent was removed by vacuum

Sources & evidence

ORD record
ord-9e12550b11bd43b189c348c8bcf57239
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07642270B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes