Triethylamine → HCID 20159919, compound

HRID 980004Notes

Reaction equation

HRID 980004 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]([NH2:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:23]1[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:33](Cl)(=[O:35])=[O:34])[C:27]=2[CH:26]=[CH:25][N:24]=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]([NH:15][S:33]([C:28]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:34])=[O:35])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33716555-Isoquinolinesulfonyl chlorideHCID 20159885HCID 20159885, compound

Product 1

HCID 20159919HCID 20159919, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

In 20 ml of a chloroform solution containing 2.23 g of 2-benzyloxycarbonylamino-1-methylethylamine and 1.2 g of triethylamine was added dropwise 20 ml of a chloroform solution containing 1.80 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 20° C. to 25° C. for two hours, and the reaction mixture solution was washed with water and dried with anhydrous magnesium sulfate. The chloroform was distilled therefrom under reduced pressure. The crystalline residue thus obtained was recrystallized from ethanol to give 2.68 g of N-(2-benzyloxycarbonylamino-1-methylethyl)-5-isoquinolinesulfonamide in a yield of 85%.

Workup

  1. temperatureunder cooling with ice
  2. washthe reaction mixture solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe chloroform was distilled
  5. customThe crystalline residue thus obtained
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c2444365e5f14126b2e34ea7cf5d467a
Source dataset
uspto-grants-1987_01
Patent number
US04634770

Reaction notes

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