Methanol → HCID 178512676, compound

HRID 2289781Notes

Reaction equation

HRID 2289781 reaction equation
C([O:5][C:6](=[O:32])[C@H:7]([CH2:27][CH2:28][C:29](=[O:31])[NH2:30])[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:26])=[CH:17][N:18]=[C:19]2[NH:22][C:23]([NH2:25])=[NH:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)(C)C.CO.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C1(C)C=CC=CC=1>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[Cl:26][C:16]1[C:15]2[C:20](=[CH:21][C:12]([S:9]([NH:8][C@H:7]([C:6]([OH:32])=[O:5])[CH2:27][CH2:28][C:29](=[O:31])[NH2:30])(=[O:11])=[O:10])=[CH:13][CH:14]=2)[C:19]([NH:22][C:23]([NH2:25])=[NH:24])=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 178451195HCID 178451195, compound

Product 1

HCID 178512676HCID 178512676, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-glutamine tert-butyl ester (15 mg, 0.03 mmol) was dissolved in trifluoroacetic acid (1 ml) and the resultant solution stirred at room temperature for 1 h, diluted with toluene and concentrated to a residue. Trituration with Et2O gave a powder to which was added MeOH and the suspension filtered. The filtrate was concentrated and then triturated with EtOAc to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-glutamine trifluoroacetate (9 mg, 0.02 mmol).

Workup

  1. concentrationconcentrated to a residue
  2. customTrituration with Et2O gave a powder to which
  3. filtrationthe suspension filtered
  4. concentrationThe filtrate was concentrated
  5. customtriturated with EtOAc

Sources & evidence

ORD record
ord-39a3340ddcd7427586ec87f027e5e553
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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