Trifluoroacetic acid → HCID 178478803, compound

HRID 2289727Notes

Reaction equation

HRID 2289727 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:22]=[CH:21][N:20]=[CH:19][CH:18]=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:22]=[CH:21][N:20]=[CH:19][CH:18]=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 178451245HCID 178451245, compound

Product 1

HCID 178478803HCID 178478803, compoundYield 58.2%

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-(4-pyridylmethyl)glycine t-butyl ester (88 mg, 0.17 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 CH2Cl2. The oily residue was dissolved in CH2Cl2 -MeOH (1.0 mL, 9:1) 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-(4-pyridylmethyl)glycine dihydrochloride (18 mg, 0.033 mmol).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customazeotroping with CH2Cl2
  3. dissolutionThe oily residue was dissolved in CH2Cl2 -MeOH (1.0 mL, 9:1)
  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-2a191ca20ecd4a00a9b2eb427e40b097
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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