Triethylamine → HCID 86592091, compound

HRID 352973Notes

Reaction equation

HRID 352973 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH2:29][CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.C(N(CC)CC)C.Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43].C(OCC)(=O)C>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 79177tert-Butyl bromoacetateHCID 11272253HCID 11272253, compound

Product 1

HCID 86592091HCID 86592091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (50 ml) was dissolved 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (240 mg), followed by the addition of triethylamine (0.28 ml) and then tert-butyl bromoacetate (0.14 ml). The resulting mixture was stirred overnight at room temperature. After concentration of the reaction mixture under reduced pressure, ethyl acetate was added to the residue. The resulting mixture was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (Φ3.0×12.0 cm, hexane:ethyl acetate 3:2), whereby the title compound (207 mg) was obtained as a colorless foam.

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column (Φ3.0×12.0 cm, hexane:ethyl acetate 3:2), whereby the title compound (207 mg)
  6. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-287e1ca178974e5fb442fcb5e3ca6b5b
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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