Methylamine → 8-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide
Reaction equation
[CH3:1][NH2:2].C([O:5][C:6]([C:8]1[C:9](=[O:33])[C:10]2[CH:15]=[N:14][C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)=[N:12][C:11]=2[N:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:26]=1)=O)C>>[CH3:1][NH:2][C:6]([C:8]1[C:9](=[O:33])[C:10]2[CH:15]=[N:14][C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)=[N:12][C:11]=2[N:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:26]=1)=[O:5]Participants
Procedure
A solution of methylamine (1N, 1 ml in methanol) was added to 2-(3-imidazol-1-yl-propylamino)-8-cyclohexyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (Example 28, Step F, 7.0 mg, 0.015 mmol). The mixture was kept in a sealed tube at 110° C. with stirring for 2 days. The solution, after cooling down to room temperature, was loaded to hplc for purification. 8-Cyclohexyl-2-(3-imidazol-1-yl-propylamino)-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methylamide was obtained as a white solid (5.5 mg, 80%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.67 (br, 1H), 9.26 (s, 1H), 8.79 (s, 1H), 7.51 (br, 1H), 7.10 (s, 1H), 6.93 (br, 1H), 5.95 (br, 1H), 5.06 (m, 1H), 4.10 (t, J=6.8 Hz, 2H), 3.50 (m, 2H), 2.98 (d, J=4.9 Hz, 3), 2.20-1.20 (m, 12H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C21H27N7O2: 410.22 (M+H). Found: 410.2.
Workup
- customThe mixture was kept in a sealed tube at 110° C.
- customto hplc for purification
Sources & evidence
- ORD record
- ord-865cc6e9e74747bfadcbd7e76272fd1f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728003B2
Reaction notes
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