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

HRID 1481189Notes

Reaction equation

HRID 1481189 reaction equation
C([O:5][C:6]([C:8]1([CH2:12][NH:13][C:14]([C:16]2[N:17]=[C:18]([C:34]#[N:35])[C:19]3[C:24]([C:25]=2[OH:26])=[CH:23][CH:22]=[C:21]([S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:20]=3)=[O:15])[CH2:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:34]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([S:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:20]=2)[C:25]([OH:26])=[C:16]([C:14]([NH:13][CH2:12][C:8]2([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][CH2:11]2)=[O:15])[N:17]=1)#[N:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 898130461-{[(1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl ester

Product 1

HCID 717362621-{[(1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-{[(1-cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl ester (58 mg), TFA (2 mL) and DCM (6 mL) was stirred at rt for 1 h; 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 (50 mg). LC MS ESI+: 434 (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-182eac41f1d349169b794bcd86b9d9ae
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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