Triethylamine → HCID 25261120, compound

HRID 538835Notes

Reaction equation

HRID 538835 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([O:12][C:13]2[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[NH2:56][C:57]1[CH:58]=[C:59]([S:63]([NH2:66])(=[O:65])=[O:64])[CH:60]=[N:61][CH:62]=1>CN(C=O)C>[S:63]([C:59]1[CH:58]=[C:57]([NH:56][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:23])([F:24])[F:1])=[CH:4][C:5]=2[O:12][C:13]2[CH:14]=[N:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=2)[CH:62]=[N:61][CH:60]=1)(=[O:65])(=[O:64])[NH2:66]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 126842595-Aminopyridine-3-sulfonamideHCID 57687707HCID 57687707, compound

Product 1

HCID 25261120HCID 25261120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-yloxy)benzoic acid (28 mg, 81 μmol), HATU (31 mg, 81 μmol), and Et3N (11 μL, 81 μmol) in DMF (1.0 mL) was stirred at room temperature for 5 min, then 5-aminopyridine-3-sulfonamide (14 mg, 81 μmol) was added. The reaction was stirred at room temperature then overnight at 70° C. The reaction was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to give N-(5-sulfamoylpyridin-3-yl)-4-(trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-yloxy)benzamide. LC/MS: m/z 507.3 (M+H)+ at 1.61 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customovernight
  2. customat 70° C
  3. customThe reaction was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-44a7d4d3006346caa371dae4bfa21be1
Source dataset
uspto-grants-2014_10
Patent number
US08865771B2

Reaction notes

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