Water → HCID 178451277, compound

HRID 2289762Notes

Reaction equation

HRID 2289762 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[CH:16][CH:17]=2)[C:12]([NH:26][C:27]([NH2:29])=[NH:28])=[N:11][CH:10]=1.Cl.NC(N)=N.[C:35](OC(=O)CNC(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)=O)([CH3:38])([CH3:37])[CH3:36].O>CS(C)=O>[C:35]([O:24][C:23](=[O:25])[CH2:22][NH:21][C:19]([C:15]1[CH:14]=[C:13]2[C:18]([C:9]([Cl:8])=[CH:10][N:11]=[C:12]2[NH:26][C:27]([NH2:29])=[NH:28])=[CH:17][CH:16]=1)=[O:20])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 18698230HCID 18698230, compoundHCID 178512656HCID 178512656, compound

Product 1

HCID 178451277HCID 178451277, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]glycine trifluoroacetate ##STR60## NaH (34 mg, 60% dispersion in mineral oil, 0.85 mmol) was added to a stirred solution of guandine hydrochloride (80 mg, 0.84 mmol) in DMSO (2 mL) at 23° C. After 30 min, N-[(1,4-dichloro-7-isoquinolinyl)carbonyl]glycine t-butyl ester (120 mg, 0.34 mmol) was added and the resultant solution heated at 90° C. for 21 h. After cooling, the mixture was poured into water (30 mL), extracted with EtOAc, and then with CH2Cl2, and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography on silica gel using CH2Cl2 -MeOH-0.880NH3 (90:10:1) as eluant to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]glycine t-butyl ester (25 mg, 0.07 mmol) as a yellow gum.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. dry with materialwith CH2Cl2, and the combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f373486ceae946aebe085a73a3b20f54
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…