Water → HCID 178451105, compound

HRID 2289764Notes

Reaction equation

HRID 2289764 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:20][C:21]([NH2:23])=[NH:22])=[N:4][CH:3]=1.Cl.NC(N)=N.O>CS(C)=O>[C:6]([O:18][C:17](=[O:19])[CH2:16][CH2:15][NH:14][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[NH:20][C:21]([NH2:23])=[NH:22])=[CH:10][CH:9]=1)=[O:13])([CH3:11])([CH3:7])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 178512652HCID 178512652, compound

Product 1

HCID 178451105HCID 178451105, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]-β-alanine ##STR61## NaH (114 mg, 60% dispersion in mineral oil, 2.85 mmol) was added portionwise to a stirred solution of guanidine hydrochloride (272 mg, 2.85 mmol) in DMSO (8 mL) and the solution was heated at 80° C. for 20 min. N-[(1,4-Dichloro-7-isoquinolinyl)carbonyl]-P-alanine t-butyl ester (420 mg, 1.14 mmol) was added and the mixture heated at 90° C. overnight. The cooled mixture was poured into water, extracted with EtOAc, and the combined organic extracts were washed with water, saturated brine, dried (Na2SO4) and evaporated in vacuo. The residue was crystallised from i-Pr2O-CH2Cl2 to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]-β-alanine t-butyl ester (190 mg, 0.48 mmol).

Workup

  1. temperaturethe mixture heated at 90° C. overnight
  2. extractionextracted with EtOAc
  3. washthe combined organic extracts were washed with water, saturated brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was crystallised from i-Pr2O-CH2Cl2

Sources & evidence

ORD record
ord-7e0a304328cd458993895a9a562e994b
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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