Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 68812098, compound
Reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][C:10](=[O:11])[CH2:9]1)=[O:7])([CH3:4])[CH3:3].CN(C(ON1N=NC2C=[CH:29][CH:30]=[N:31][C:26]1=2)=[N+](C)C)C.[F:34][P-](F)(F)(F)(F)F>C(Cl)Cl>[C:2]([O:5][C:6]([N:8]1[CH2:9][C:10](=[O:11])[CH2:12][C@H:13]1[C:14]([N:31]1[CH2:30][CH:29]([F:34])[CH2:26]1)=[O:16])=[O:7])([CH3:1])([CH3:3])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-tert-Boc-4-oxo-L-proline (917 mg, 4 mmol), the title compound of Step 2 (446 mg, 4 mmol), and HATU (1.673 g, 4.4 mmol) were mixed under nitrogen in anhydrous methylene chloride. The solution was cooled in an ice bath before the addition of DIEA (1.4 mL, 8 mmol). The reaction mixture was allowed to warm to RT and stirred overnight. Saturated sodium bicarbonate was added, the phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic portions were washed with brine and dried over magnesium sulfate. The crude product (2.11 g) was purified by chromatography (Biotage® Flash 40S, 95:5 EtOAc:MeOH) to give the title product as light pink foam (1.06 g, 92%). MS m/z 287.3 (MH+).
Sources & evidence
- ORD record
- ord-4c3be559aa0a49fbb6239e7995f1a3ef
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465732B2
Reaction notes
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