Triethylamine → HCID 22502952, compound

HRID 1814508Notes

Reaction equation

HRID 1814508 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:32]([S:34]([Cl:37])(=[O:36])=[O:35])#[CH:33]>O1CCCC1>[ClH:37].[CH2:32]([S:34]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:8]=2)[CH2:2][CH2:3]1)(=[O:36])=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22502866HCID 22502866, compoundHCID 22503460HCID 22503460, compound

Product 1

HCID 22502952HCID 22502952, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Piperazinyl-3-(4-methoxyphenyl)isoquinoline (140 mg) was dissolved in tetrahydrofuran (2 ml), followed by the addition of triethylamine (0.12 ml) and ethynylsulfonyl chloride (0.08 ml), and the mixture was reacted for 2 hr. The reaction solution was partitioned between ethyl acetate and a 2N aqueous solution of sodium hydroxide. The resulting organic layer was washed with water and brine and dried. The resulting product was recrystallized from hexane/ethyl acetate, to give the title compound (139 mg, yield; 77%). The resulting compound was converted into an oxalate in a conventional manner, to give the oxalate of the title compound as white crystals.

Workup

  1. customthe mixture was reacted for 2 hr
  2. customThe reaction solution was partitioned between ethyl acetate
  3. washThe resulting organic layer was washed with water and brine
  4. customdried
  5. customThe resulting product was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-fb193e902520449fb0feb958ef7d764c
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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