Ethanolamine → HCID 178512660, compound

HRID 2289782Notes

Reaction equation

HRID 2289782 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]3[CH2:28][CH2:27][CH2:26][C@@H:22]3[C:23](O)=[O:24])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[C:11]([NH:29][C:30]([NH2:32])=[NH:31])=[N:10][CH:9]=1.[CH2:33]([CH2:35][NH2:36])[OH:34]>C(Cl)Cl.CN(C=O)C>[NH3:10].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([N:21]3[CH2:28][CH2:27][CH2:26][C@@H:22]3[C:23]([NH:36][CH2:35][CH2:33][OH:34])=[O:24])(=[O:19])=[O:20])=[CH:15][CH:16]=2)[C:11]([NH:29][C:30]([NH2:32])=[NH:31])=[N:10][CH:9]=1

Participants

7

Reactant 3

HCID 700EthanolamineHCID 65578Oxalyl chlorideHCID 178512661HCID 178512661, compound

Product 2

HCID 222AmmoniaHCID 178512660HCID 178512660, compoundYield 127.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

##STR81## Oxalyl chloride (40 μl, 0.46 mmol) was added to a solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-D-proline (100 mg, 0.23 mmol) in CH2Cl2 (10 ml), followed by DMF (1 drop), and the reaction stirred at room temperature for 30 min. The mixture was evaporated in vacuo and azeotroped with toluene. The residue was dissolved in CH2Cl2 (5 ml), and added to a solution of ethanolamine (17 μl, 0.28 mmol) in CH2Cl2 (5 ml), the reaction stirred at room temperature for 2 h, then concentrated in vacuo. The crude product was purified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0.880 NH3 (95:5:0.5 to 90:10:1) to afford (2R)-1-({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)-N-(2-hydroxyethyl)-2-pyrrolidinecarboxamide (65 mg, 0.147 mmol) as a yellow foam.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customazeotroped with toluene
  3. dissolutionThe residue was dissolved in CH2Cl2 (5 ml)
  4. stirringthe reaction stirred at room temperature for 2 h
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0

Sources & evidence

ORD record
ord-b66805d8c354407c865a3930398ae753
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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