Triethylamine → HCID 9843932, compound

HRID 2084847Notes

Reaction equation

HRID 2084847 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=O)[NH:3]1.C([N:17](CC)CC)C.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[C:23]#[C:24][CH3:25].C1COCC1.[OH2:42]>C(OCC)(=O)C>[OH:42][NH:17][C:12]([CH:4]1[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][N:3]1[S:33]([C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:22][C:23]#[C:24][CH3:25])=[CH:28][CH:29]=1)(=[O:35])=[O:34])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochlorideHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 9843932HCID 9843932, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.00 g (9.359 mmol) of 1,2,3,4-tetrahyro-3-isoquinolinecarboxylic acid hydrochloride in 70 mL of THF/water (1:1) was added 10.0 mL of triethylamine followed by 2.30 g (9.407 mmol) of 4-but-2-ynyloxy-benzenesulfonyl chloride and the reaction was stirred overnight at room temperature. The reaction mixture was then diluted with ethyl acetate and the organic layer was washed with water and 5% HCl solution, dried over MgSO4, filtered and concentrated in vacuo. The solid residue was washed with ether/hexanes (1:1) to provide 2.73 g (76%) of the sulfonamide as a pale yellow solid. Electrospray Mass Spec 385.9 (M+H)+.

Workup

  1. washthe organic layer was washed with water and 5% HCl solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe solid residue was washed with ether/hexanes (1:1)

Sources & evidence

ORD record
ord-0672e76f984a48fb8ab2b015de432aa1
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

Loading…