tert-Butyl piperazine-1-carboxylate → HCID 68550944, compound

HRID 1868117Notes

Reaction equation

HRID 1868117 reaction equation
Cl[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:15][CH2:14]3)(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.C(O[Na])(C)(C)C.[C:37]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:40]([O:39][C:37]([N:44]1[CH2:49][CH2:48][N:47]([C:2]2[CH:30]=[CH:29][C:5]3[S:6][C:7]([S:10]([N:13]4[CH2:18][CH2:17][N:16]([C:19]5[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=5)[CH2:15][CH2:14]4)(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=3[CH:3]=2)[CH2:46][CH2:45]1)=[O:38])([CH3:43])([CH3:41])[CH3:42]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 68549409HCID 68549409, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 68550944HCID 68550944, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

1-(5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl)-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine (142.5 mg, 0.3 mmol), Pd2(dba)3 (13.7 mg, 0.015 mmol), t-BuONa (82.7 mg, 0.84 mmol) and the ligand (9 mg, 0.03 mmol) were mixed in a sealed tube which was flushed with N2. To this was added tolene (2 mL) and then 1-BOC-piperazine (67.1 mg, 0.36 mmol). The resultant mixture was heated at 80° C. for 3 hours. The solvent was removed under vacuum and the crude product was purified with flash column chromatography to yield 4-{3-methyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-5-yl}-piperazine-1-carboxylic acid tert-butyl ester 68% yield (128 mg) as white solid.

Workup

  1. customwas flushed with N2
  2. additionTo this was added tolene (2 mL)
  3. customThe solvent was removed under vacuum
  4. customthe crude product was purified with flash column chromatography

Sources & evidence

ORD record
ord-3431b5e1a1b440bea9074902eab4af8a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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