Triethylamine → HCID 89924300, compound

HRID 1500904Notes

Reaction equation

HRID 1500904 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[F:10][C:11]([F:17])([F:16])[CH2:12][C:13](O)=[O:14].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:13](=[O:14])[CH2:12][C:11]([F:17])([F:16])[F:10])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 938984-Chloro-2-fluoroanilineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89924300HCID 89924300, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-2-fluoroaniline (3 g, 20.7 mmol), 3,3,3-trifluoropropanoic acid (2.6 g, 20.7 mmol) and Et3N (5.8 mL) were dissolved in 50 mL of DCM. To this solution was added HATU (8.6 g, 22.7 mmol) slowly and then stirred overnight. The organic phases was washed with aq. NH4Cl (50 mL), NaHCO3 solution (50 mL) and brine (100 mL). The combined organic phases were evaporated and purified by column chromatography (PE/EA=5/1) to give N-(4-chloro-2-fluorophenyl)-3,3,3-trifluoropropanamide which was pure enough for next step. (4.7 g, yield: 90%) was a yellow solid. MS obsd. (ESI+) [(M+H)+] 256.

Workup

  1. washThe organic phases was washed with aq. NH4Cl (50 mL), NaHCO3 solution (50 mL) and brine (100 mL)
  2. customThe combined organic phases were evaporated
  3. custompurified by column chromatography (PE/EA=5/1)

Sources & evidence

ORD record
ord-7b36a96c7a614d1bb4529cfeccba72bf
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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