Trifluoroacetic acid → HCID 178478802, compound

HRID 2289726Notes

Reaction equation

HRID 2289726 reaction equation
C(C(O)=O)(F)(F)F.C([O:12][C:13](=[O:41])[CH2:14][N:15]([S:23]([C:26]1[CH:35]=[C:34]2[C:29]([C:30]([Cl:40])=[CH:31][N:32]=[C:33]2[NH:36][C:37]([NH2:39])=[NH:38])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)(C)(C)C>C(Cl)Cl>[ClH:40].[ClH:40].[Cl:40][C:30]1[C:29]2[C:34](=[CH:35][C:26]([S:23]([N:15]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][C:13]([OH:41])=[O:12])(=[O:24])=[O:25])=[CH:27][CH:28]=2)[C:33]([NH:36][C:37]([NH2:39])=[NH:38])=[N:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451243HCID 178451243, compound

Product 1

HCID 178478802HCID 178478802, compoundYield 129%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

CF3CO2H (1.0 mL) was added to a stirred solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(3-pyridylmethyl)glycine t-butyl ester (100 mg, 0.20 mmol) in CH2Cl2 (1.0 mL) and the mixture was stirred at 23° C. for 3.5 h. The solvents were evaporated in vacuo, azeotroping with PhMe and CH2Cl2. The oily residue was dissolved in EtOAc and a solution of EtOAc saturated with HCl (3.0 mL) was added which gave a precipitate. The white solid was collected by filtration and dried to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(3-pyridylmethyl)glycine dihydrochloride (48 mg, 0.086 mmol).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customazeotroping with PhMe and CH2Cl2
  3. dissolutionThe oily residue was dissolved in EtOAc
  4. additiona solution of EtOAc saturated with HCl (3.0 mL) was added which
  5. customgave a precipitate
  6. filtrationThe white solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a0c4db7e90784e26bca3f50868a244d9
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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