Methylamine → 1-[6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid methylamide
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@@H:20]3[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[C@@H:22]([OH:30])[C@H:21]3[OH:31])=[C:13]([NH:32][CH:33]([C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=3)[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[N:12]=2)[CH:10]=1)=O)C.[CH3:50][NH2:51]>>[CH3:50][NH:51][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[C@@H:20]3[CH2:24][C@H:23]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[C@@H:22]([OH:30])[C@H:21]3[OH:31])=[C:13]([NH:32][CH:33]([C:42]3[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=3)[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[N:12]=2)[CH:10]=1)=[O:3]Participants
3
Reactant 2
Product 1
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 1-[6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 168, step 3) (0.2 g, 0.298 mmol) and 40% aqueous methyl amine solution (5 ml) is heated to 65° C. for 12 h. The reaction mixture concentrated in vacuo and purification of the crude residue by chromatography on silica eluting with 3% methanol in chloroform yields the title compound. LC-MS (0.1% formic acid, acetonitrile): 656 (MH+).
Workup
- concentrationThe reaction mixture concentrated in vacuo and purification of the crude residue by chromatography on silica eluting with 3% methanol in chloroform
Sources & evidence
- ORD record
- ord-1132fbead4e94e6da3710acfbf6d659e
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258141B2
Reaction notes
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