Benzoyl chloride → HCID 68623959, compound

HRID 1783406Notes

Reaction equation

HRID 1783406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@@H:19]2[CH2:25][C:24]([F:27])([F:26])[CH2:23][CH2:22][NH:21][C:20]2=[O:28])[CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:36]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][N:11]([C@@H:19]2[CH2:25][C:24]([F:27])([F:26])[CH2:23][CH2:22][NH:21][C:20]2=[O:28])[S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:18][CH2:17]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68623756HCID 68623756, compound

Product 1

HCID 68623959HCID 68623959, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-N-piperidin-4-ylmethyl-benzenesulfonamide (0.04 g, 0.09 mmol) and triethylamine (19 mg, 0.18 mmol) were dissolved in dichloromethane (1.5 ml). Then benzoyl chloride (0.018 g, 0.13 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified over silica gel (heptane/ethyl acetate 1:1) to yield 29 mg (58%) of the title compound;

Workup

  1. customThe reaction mixture was partitioned between aqueous sodium bicarbonate solution and ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over silica gel (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-9fca5523fdbe41458e37906910fc45ca
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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