HCID 89812899, compound → 3-{[7-(2-Chloro-4-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid

HRID 1481109Notes

Reaction equation

HRID 1481109 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]=[CH:28][C:27]([F:30])=[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]=[C:27]([F:30])[CH:28]=[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

3

Reactant 1

HCID 89812899HCID 89812899, compound

Product 1

HCID 717364373-{[7-(2-Chloro-4-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acidYield 68.1%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of 3-{[7-(2-chloro-4-fluoro-phenoxy)-1-cyano-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid tert-butyl ester (40 mg, 0.08) in (½) TFA/CH2Cl2 (3 mL) was stirred at room temperature for 4 h. Reaction mixture was concentrated. The residue was dissolved in water (30 mL) and the pH was adjusted to 10 by 1 N NaOH. It was then acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 24 mg (0.053 mmol) in 66% yield. LC-MS ESI−: 456.05 (M−1)−.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionThe residue was dissolved in water (30 mL)
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-de368fa1fb76422e937ffb0d8795ed8d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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