Triethylamine → HCID 90315065, compound

HRID 1484195Notes

Reaction equation

HRID 1484195 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:15]=2[C:16]([OH:18])=O)=[C:11]([CH3:29])[CH:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:54][C:55]1[CH:67]=[CH:66][C:58]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])=[CH:57][CH:56]=1>CN(C=O)C>[F:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][C:15]=2[C:16]([NH:54][C:55]2[CH:67]=[CH:66][C:58]([C:59]([O:61][C:62]([CH3:63])([CH3:64])[CH3:65])=[O:60])=[CH:57][CH:56]=2)=[O:18])=[C:11]([CH3:29])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90315045HCID 90315045, compound

Product 1

HCID 90315065HCID 90315065, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (177.4 ml, 1.27 mmol) was added to a solution of 2-(4-fluoro-2-methylphenoxy)-5-(trifluoromethyl)benzoic acid (100 mg, 0.32 mmol), HATU (121 mg, 0.32 mmol) and tert-butyl 4-aminobenzoate (61.49 mg, 0.32 mmol) in DMF (1 mL) and the reaction was stirred at room temperature overnight. The reaction was filtered and purified by reverse phase LC-MS using a gradient of acetonitrile in water (10-99%) and HCl as a modifier to yield tert-butyl 4-(2-(4-fluoro-2-methylphenoxy)-5-(trifluoromethyl)benzamido)benzoate (43.8 mg, 28%). ESI-MS m/z calc. 489.16. found 490.3 (M+1)+; Retention time: 2.46 minutes (3 minutes run).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase LC-MS

Sources & evidence

ORD record
ord-e038fc6fc9e94c8994f6f23e222f2aa4
Source dataset
uspto-grants-2016_08
Patent number
US09421196B2

Reaction notes

Loading…