Trifluoroacetic acid → HCID 71735617, compound

HRID 1481212Notes

Reaction equation

HRID 1481212 reaction equation
C([O:5][C:6](=[O:35])[CH:7]([CH:32]1[CH2:34][CH2:33]1)[CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]([C:30]#[N:31])[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][CH:27]=[CH:26][CH:25]=1)[CH:16]=2)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[C:30]([C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:16]=2)[C:21]([OH:22])=[C:12]([C:10]([NH:9][CH2:8][CH:7]([CH:32]2[CH2:34][CH2:33]2)[C:6]([OH:35])=[O:5])=[O:11])[N:13]=1)#[N:31]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89812917HCID 89812917, compound

Product 1

HCID 71735617HCID 71735617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[(1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-2-cyclopropyl-propionic acid tert-butyl ester (65 mg) and TFA (2 mL) in DCM (2 mL) was stirred at rt for 2 h. The mixture was subsequently concentrated and resulting residue was dissolved in EtOAc, washed with water, diluted NaCl solution and dried over anhydrous sodium sulfate, filtered, concentrated and solids were treated with hot DCM/hexanes (1:1 by volume); solids after cooling were collected via filtration, giving desired product after air-drying as white solids (40 mg). LC-MS ESI+: 418 (M+1)+.

Workup

  1. concentrationThe mixture was subsequently concentrated
  2. customresulting residue
  3. washwashed with water, diluted NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionsolids were treated with hot DCM/hexanes (1:1 by volume)
  8. temperaturesolids after cooling
  9. filtrationwere collected via filtration

Sources & evidence

ORD record
ord-fd12192dab36461798266696022c49fc
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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