Sodium Hydroxide → HCID 178512668, compound

HRID 2289795Notes

Reaction equation

HRID 2289795 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:26][CH2:27][O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[C:16]3([C:21]([O:23]CC)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:35][C:36]([NH2:38])=[NH:37])=[N:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15]([CH2:26][CH2:27][O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[C:16]3([C:21]([OH:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:13])=[O:14])=[CH:9][CH:10]=2)[C:5]([NH:35][C:36]([NH2:38])=[NH:37])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470257HCID 178470257, compound

Product 1

HCID 178512668HCID 178512668, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylate in MeOH (5 ml), was heated to 75° C., NaOH solution (1 ml, 2N, 2 mmol) added, and the reaction stirred at 50° C. for 48 h. The cooled reaction mixture was concentrated in vacuo , to remove the MeOH, and the remaining aqueous solution acidifed to pH 6 using 1N HCl. The resulting precipitate was filtered, washed with water, and the filtrate extracted with EtOAc. The combined organic extracts were dried (MgSO4), and evaporated in vacuo to give 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylic acid (9 mg, 0.017 mmol) as a pale yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto remove the MeOH
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. extractionthe filtrate extracted with EtOAc
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4fd8c6e6fb5249ecba1290a77f96a0f8
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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