Trifluoroacetic acid → HCID 131736767, compound

HRID 1485900Notes

Reaction equation

HRID 1485900 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:18])[CH:14]=2)[CH:9]1[C:19](=[O:29])[NH:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[F:28])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([F:27])[C:21]=1[NH:20][C:19]([CH:9]1[C:10]2[C:15](=[CH:14][C:13]([Cl:18])=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041098HCID 90041098, compound

Product 1

HCID 131736767HCID 131736767, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL pear-shaped flask, 6-chloro-1-(2,6-difluoro-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.6 g, 1.42 mmol, Eq: 1.00) was combined with DCM (25 mL) to give a light brown solution. TFA (4.85 g, 3.28 mL, 42.6 mmol, Eq: 30) was added. After 1 h, the reaction was concentrated, the residue dissolved in EtOAc and the mixture washed with 1 N NaOH and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford 0.3937 g 6-chloro-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid (2,6-difluoro-phenyl)-amide as a brown oil which was used without purification. 86.0% MS m/z 323.0 (M+H)

Workup

  1. customto give a light brown solution
  2. concentrationthe reaction was concentrated
  3. dissolutionthe residue dissolved in EtOAc
  4. washthe mixture washed with 1 N NaOH and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90f4a0ecbb034fd8b21f75695bef04e1
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

Loading…