Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 52919853, compound

HRID 1846104Notes

Reaction equation

HRID 1846104 reaction equation
[C:1]([C:5]([NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:18]([F:21])([F:20])[F:19])=[C:13]([CH:17]=1)[C:14](O)=[O:15])=[O:6])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:46][C:47]1[CH:48]=[CH:49][C:50]([O:63][CH2:64][CH:65]([F:67])[F:66])=[C:51]([CH:62]=1)[C:52]([NH:54][C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1)=[O:53]>C1COCC1>[F:67][CH:65]([F:66])[CH2:64][O:63][C:50]1[CH:49]=[CH:48][C:47]([NH:46][C:14](=[O:15])[C:13]2[CH:17]=[C:9]([CH2:8][NH:7][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[O:6])[CH:10]=[CH:11][C:12]=2[C:18]([F:20])([F:19])[F:21])=[CH:62][C:51]=1[C:52]([NH:54][C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1)=[O:53]

Participants

5

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 58483224HCID 58483224, compoundHCID 67116376HCID 67116376, compound

Product 1

HCID 52919853HCID 52919853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(tert-butylcarbonylamino)methyl-2-trifluoromethyl-benzoic acid (50 mg; 0.13 mmol) HATU (53.8 mg, 0.14 mmol) and TEA (0.066 mL 0.47 mmol) in 2 mL THF was stirred for 15 min at rt. 5-Amino-N-(4-bromo-phenyl)-2-(2,2-difluoro-ethoxy)-benzamide (40.8 mg; 0.13 mmol) was added and it was stirred over night. The solvent was evaporated and the residue was purified by prep HPLC.

Workup

  1. stirringit was stirred over night
  2. customThe solvent was evaporated
  3. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-0b6a200f86ab41b5a671068e47ed41f1
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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