Dimethylamine → HCID 178484501, compound

HRID 2289793Notes

Reaction equation

HRID 2289793 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([N:16](CCO)[C:17]3([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]3)(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([NH:30][C:31]([NH2:33])=[NH:32])=[N:5][CH:4]=1.Cl.ClC1C2C(=CC(S(NC3(C(O)=O)CCCC3)(=O)=O)=CC=2)C(NC(N)=N)=NC=1.CNC>C(Cl)Cl.CN(C=O)C>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][C:17]3([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]3)(=[O:14])=[O:15])=[CH:10][CH:11]=2)[C:6]([NH:30][C:31]([NH2:33])=[NH:32])=[N:5][CH:4]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 178479402HCID 178479402, compoundHCID 178484496HCID 178484496, compound

Product 1

HCID 178484501HCID 178484501, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1-[({4-Chloro-1-guanidino-7-isoquinolinyl}sulphonyl)(2-hydroxyethyl)amino]-N,N-dimethylcyclopentanecarboxamide hydrochloride ##STR97## Oxalyl chloride (3.5 ml, 4.0 mmol) was added to a suspension of N-({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)cycloleucine hydrochloride (870 mg, 1.94 mmol) in CH2Cl2 (100 ml), followed by DMF (5 drops), and the reaction stirred at room temperature for 2 h. The solution was concentrated in vacuo and azeotroped with toluene to give a yellow gum. This was dissolved in CH2Cl2 (100 ml), the solution cooled to -20° C., and cooled N,N-dimethylamine (10 ml) added. The reaction was allowed to warm to room temperature with stirring, over 30 min, then concentrated in vacuo, and the residue azeotroped with toluene. The crude product was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880 NH3 (95:5:0.5) as eluant, and crystallised from MeOH to afford to afford 1-[({4-chloro-1-guanidino-7-isoquinolinyl}sulphonyl)amino]-N,N-dimethylcyclopentanecarboxamide (302 mg, 0.69 mmol) as a yellow solid. mp. 264-268° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customazeotroped with toluene
  3. customto give a yellow gum
  4. temperaturethe solution cooled to -20° C.
  5. additionadded
  6. temperatureto warm to room temperature
  7. stirringwith stirring, over 30 min
  8. concentrationconcentrated in vacuo
  9. customthe residue azeotroped with toluene
  10. customThe crude product was purified by column chromatography upon silica gel
  11. custom880 NH3 (95:5:0.5) as eluant, and crystallised from MeOH
  12. customto afford

Sources & evidence

ORD record
ord-f4ea5742d51144a89a5387fc6233e72c
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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