Triethylamine → HCID 21094222, compound

HRID 1350329Notes

Reaction equation

HRID 1350329 reaction equation
CCN(CC)CC.[N:8]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[Cl:21][C:22]1[S:26][C:25]([NH:27][C:28]([CH:30]([C:38]2[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=2)[CH2:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:29])=[N:24][CH:23]=1>CC(N(C)C)=O>[Cl:21][C:22]1[S:26][C:25]([NH:27][C:28]([CH:30]([C:38]2[CH:39]=[CH:40][C:41]([S:44]([N:11]3[CH2:12][CH2:13][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:10]3)(=[O:46])=[O:45])=[CH:42][CH:43]=2)[CH2:31][CH:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[O:29])=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21094064HCID 21094064, compound

Product 1

HCID 21094222HCID 21094222, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

NEt3 (278 μL, 2.0 mmol) and tert-butyl piperazine-1-carboxylate (373 mg, 2.0 mmol) were added to a stirred solution of 4-[1-(5-chlorothiazol-2-ylcarbamoyl)-2-(tetrahydropyran-4-yl)ethyl]benzenesulfonyl chloride (Preparation 60, 449 mg, 1.0 mmol) in anhydrous DMAc (4 mL). The mixture was stirred for 16 h, then the solvents were removed in vacuo. The residue was dissolved in EtOAc (50 mL) to give a solution that was washed with H2O (15 mL), saturated aqueous Na2CO3 (15 mL), and brine (15 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 7:3 to 1:1) gave tert-butyl 4-{4-[1-(5-chlorothiazol-2-ylcarbamoyl)-2-(tetrahydropyran-4-yl)ethyl]benzenesulfonyl}piperazine-1-carboxylate: m/z (ES+)=599.5 [M+H]+. A solution of this compound (189 mg, 316 μmol) in CH2Cl2-TFA (1:1, 7 mL) was stirred for 1 h. The solvents were evaporated off under reduced pressure, then the residue was triturated with Et2O. The product was collected, washed with Et2O, and air-dried to furnish the trifluoroacetate salt of the title compound: RTA=2.64 min; m/z (ES+)=499.3 [M+H]+.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. customto give a solution that
  4. washwas washed with H2O (15 mL), saturated aqueous Na2CO3 (15 mL), and brine (15 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration, solvent evaporation, and column chromatography (IH-EtOAc, 7:3 to 1:1)

Sources & evidence

ORD record
ord-e7bf0e99ae2e4b208077676aca9c3082
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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