Trifluoroacetic acid → 3-{[7-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid

HRID 1480995Notes

Reaction equation

HRID 1480995 reaction equation
C([O:5][C:6](=[O:36])[C:7]([CH3:35])([CH3:34])[CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]([C:32]#[N:33])[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[C:17]([O:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[Cl:31])[CH:16]=2)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:31][C:25]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=1[O:23][C:17]1[CH:16]=[C:15]2[C:20]([C:21]([OH:22])=[C:12]([C:10]([NH:9][CH2:8][C:7]([CH3:35])([CH3:34])[C:6]([OH:36])=[O:5])=[O:11])[N:13]=[C:14]2[C:32]#[N:33])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 898130243-{[7-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl ester

Product 1

HCID 898130683-{[7-(2-Chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-{[7-(2-chloro-5-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl ester (19 mg), TFA (1 mL) and DCM (2 mL) was stirred at rt overnight; then concentrated, the residue was dissolved in water and added 2 M HCl solution, solids were collected via filtration, washed with water and air dried to give the desired product (17 mg). LC MS ESI+: 458 (M+1)+.

Workup

  1. concentrationthen concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionadded 2 M HCl solution, solids
  4. filtrationwere collected via filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-1492cc71b800440bbcdcb4aea74e1e67
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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