Trifluoroacetic acid → HCID 178479408, compound

HRID 2289757Notes

Reaction equation

HRID 2289757 reaction equation
C(C(O)=O)(F)(F)F.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:22][C@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[C:29]([O:31]C(C)(C)C)=[O:30])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[C:12]([NH:36][C:37]([NH2:39])=[NH:38])=[N:11][CH:10]=1>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:22][C@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[C:29]([OH:31])=[O:30])(=[O:20])=[O:21])=[CH:16][CH:17]=2)[C:12]([NH:36][C:37]([NH2:39])=[NH:38])=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451140HCID 178451140, compound

Product 1

HCID 178479408HCID 178479408, compoundYield 35,714.301%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

CF3CO2H (3.0 mL) was added to a stirred solution of t-butyl (±)-cis-2-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate (66 mg, 0.14 mmol) in CH2Cl2 (3.0 mL) and the mixture was stirred at 23° C. for 6 h. The solvents were evaporated in vacuo, azeotroping CH2Cl2 (×3). The residue was dissolved in EtOAc and a solution of HCl in Et2O (200 μL, 1.0 M) was added which gave a precipitate. The white solid was collected by filtration and dried to give (±)-cis-2-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylic acid hydrochloride (35 mg, 0.069 25 mmol).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customazeotroping CH2Cl2 (×3)
  3. dissolutionThe residue was dissolved in EtOAc
  4. additiona solution of HCl in Et2O (200 μL, 1.0 M) was added which
  5. customgave a precipitate
  6. filtrationThe white solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-5fd4a31cc20642df9a94efd0ac170796
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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