Triethylamine → HCID 66727319, compound

HRID 1845964Notes

Reaction equation

HRID 1845964 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=O)[O:9]CC.[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24]([S:28]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[CH:37]=[N+:36]([O-])[CH:35]=[CH:34]3)(=[O:30])=[O:29])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>CO>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][N:24]([S:28]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[C:37]([O:9][CH3:8])=[N:36][CH:35]=[CH:34]3)(=[O:30])=[O:29])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66726990HCID 66726990, compound

Product 1

HCID 66727319HCID 66727319, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 mL of triethylamine and 0.1 mL of ethyl chlorocarbonate were added dropwise with stirring at 0° C. to a methanol (5 mL) solution of 300 mg of 6-(4-tert-butoxycarbonyl-1,4-diazepan-1-ylsulfonyl)isoquinoline 2-oxide, and the mixture was then stirred at room temperature for 3 hours. After the completion of reaction, the reaction solvent was distilled off under reduced pressure. To the obtained residue, 20 mL of ethyl acetate was added, and the deposited insoluble matter was removed by filtration. The filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 110 mg of the compound of interest as a white crystal (36%).

Workup

  1. customAfter the completion of reaction
  2. distillationthe reaction solvent was distilled off under reduced pressure
  3. additionTo the obtained residue, 20 mL of ethyl acetate was added
  4. customthe deposited insoluble matter was removed by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-d9a2b0ae18264695878dac50da085558
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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