HCID 59625273, compound → HCID 59625433, compound
Reaction equation
[N:1]1([C:5]([C@@H:7]2[CH2:12][C@H:11]([N:13]([C:18]([C:20]3[C:21]([NH:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[N:22][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[N:24][CH:25]=3)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)=[O:6])[CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.Cl>[N:1]1([C:5]([C@H:7]2[CH2:8][NH:9][CH2:10][C@@H:11]([N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:18]([C:20]3[C:21]([NH:30][CH2:31][CH2:32][CH2:33][O:34][CH3:35])=[N:22][C:23]([C:26]([CH3:28])([CH3:29])[CH3:27])=[N:24][CH:25]=3)=[O:19])[CH2:12]2)=[O:6])[CH2:2][CH2:3][CH2:4]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl (3R,5S)-3-(azetidin-1-ylcarbonyl)-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (94 mg) was dissolved in 4 M hydrogen chloride-ethyl acetate (3 ml), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to reversed-phase preparative HPLC. Aqueous sodium hydrogen carbonate was added to the object fraction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object compound (33 mg).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionAqueous sodium hydrogen carbonate was added to the object fraction
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b2376de9f1784561950b8d58e2acc387
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329691B2
Reaction notes
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