Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86648211, compound

HRID 2384058Notes

Reaction equation

HRID 2384058 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:8]([OH:10])=O)=[CH:6][N:7]=1)[CH3:2].Cl.[NH2:12][C@H:13]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)=[CH:25][CH:24]=1)[CH2:14][CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[Cl:35][C:31]1[CH:30]=[C:29]([C:26]2[CH:27]=[CH:28][C:23]([CH2:22][C@@H:13]([NH:12][C:8]([C:5]3[O:4][C:3]([CH2:1][CH3:2])=[N:7][CH:6]=3)=[O:10])[CH2:14][CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:24][CH:25]=2)[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 212849102-Ethyloxazole-5-carboxylic acidHCID 67505770HCID 67505770, compound

Product 1

HCID 86648211HCID 86648211, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-ethyloxazole-5-carboxylic acid (95 mg, 0.68 mmol) in DMF (2 mL) and DCM (2 mL) is added (4S)-ethyl 4-amino-5-(3′-chlorobiphenyl-4-yl)-2-methylpentanoate hydrochloride (215 mg, 0.56 mmol), HATU (321 mg, 0.84 mmol), and TEA (392 μL, 2.81 mmol). After stirring for 2 hours, the reaction is quenched with H2O, and the crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN) to give (4S)-ethyl 5-(3′-chlorobiphenyl-4-yl)-4-(2-ethyloxazole-5-carboxamido)-2-methylpentanoate (264 mg), HPLC retention time=0.71 minutes (condition B); MS (m+1)=469.3.

Workup

  1. customthe reaction is quenched with H2O
  2. additionthe crude is diluted with EtOAc
  3. washthe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue is purified by RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN)

Sources & evidence

ORD record
ord-2b9152bdaf6247a5963be4f7bf0bcabe
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

Loading…