Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 78320720, compound

HRID 2201939Notes

Reaction equation

HRID 2201939 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[Si](C)(C)[N:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[C:57]([O:59][Si](C)(C)C)=[O:58]>C1COCC1.C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([N:52]3[CH2:56][CH2:55][CH2:54][C@H:53]3[C:57]([OH:59])=[O:58])=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=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 11076171HCID 11076171, compoundHCID 76286162HCID 76286162, compound

Product 1

HCID 78320720HCID 78320720, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid (15 mg, 0.044 mmol), TEA (0.019 mL, 0.133 mmol), and HATU (25.4 mg, 0.067 mmol) in THF (0.5 mL) and DCM (0.500 mL) was added (S)-trimethylsilyl 1-(trimethylsilyl)pyrrolidine-2-carboxylate (23.07 mg, 0.089 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated and the residue purified by HPLC to give the title compound. LCMS m/z=435.4 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-89e81615fb214800bf0705fcc383e783
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

Loading…