Trifluoroacetic acid → 2-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acid

HRID 1480952Notes

Reaction equation

HRID 1480952 reaction equation
C([O:5][C:6](=[O:35])[CH:7]([CH2:11][NH:12][C:13]([C:15]1[N:16]=[C:17]([C:33]#[N:34])[C:18]2[C:23]([C:24]=1[OH:25])=[CH:22][CH:21]=[C:20]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:19]=2)=[O:14])[CH2:8][CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:33]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:19]=2)[C:24]([OH:25])=[C:15]([C:13]([NH:12][CH2:11][CH:7]([CH2:8][CH2:9][CH3:10])[C:6]([OH:35])=[O:5])=[O:14])[N:16]=1)#[N:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 898131862-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acid tert-butyl ester

Product 1

HCID 898131112-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acidYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-{[(1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-pentanoic acid tert-butyl ester (44 mg), TFA (2 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 (27 mg). LC MS ESI+: 420 (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-a6bd84dfef7b4634b68a0e2219425e55
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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