Ammonia → 8-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

HRID 12353Notes

Reaction equation

HRID 12353 reaction equation
C(O[C:4]([C:6]1[C:7](=[O:31])[C:8]2[CH:13]=[N:12][C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)=[N:10][C:9]=2[N:23]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:24]=1)=[O:5])C.[NH3:32]>CO>[CH:25]1([N:23]2[C:9]3[N:10]=[C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)[N:12]=[CH:13][C:8]=3[C:7](=[O:31])[C:6]([C:4]([NH2:32])=[O:5])=[CH:24]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 685836918-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 160495168-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (4.5 mg, 0.011 mmol) was added to 1.0 mL of 7 N ammonia in methanol. The mixture was stirred in a sealed tube at room temperature overnight. The solvent was evaporated to leave a white solid of 8-cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide (4.0 mg, 95%). 1H NMR (400 MHz, CDCl3/CD3OD (20:1 v/v)) δ (ppm): 9.18 (s), 8.74 (s), 7.15 (br, 1H), 7.02 (br, 1H), 6.92 (br, 1H), 5.02 (m, 1H), 4.06 (t, J=6.6 Hz, 2H), 3.43 (br, 2H), 2.17 (m, 2H), 2.00-1.30 (br, 10H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C20H25N7O2: 396.21 (M+H). Found: 396.2.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7501ff3274a64db19fe67e0d2b6967e4
Source dataset
uspto-grants-2010_06
Patent number
US07728003B2

Reaction notes

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