Triethylamine → HCID 11755470, compound

HRID 1296356Notes

Reaction equation

HRID 1296356 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:12]([CH3:21])[C:11]([CH:22]2[O:27][CH2:26][CH2:25][NH:24][CH2:23]2)=[N:10]1.C(N(CC)CC)C.[CH:35]([S:38](Cl)(=[O:40])=[O:39])([CH3:37])[CH3:36]>ClCCl>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[Cl:2])[N:10]=[C:11]([CH:22]3[O:27][CH2:26][CH2:25][N:24]([S:38]([CH:35]([CH3:37])[CH3:36])(=[O:40])=[O:39])[CH2:23]3)[C:12]=2[CH3:21])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 69416303HCID 69416303, compound

Product 1

HCID 11755470HCID 11755470, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazol-3-yl]-morpholine hydrochloride 5A-2 (75 mg, 0.18 mmol) and triethylamine (49 μL, 0.36 mmol) in dichloromethane (0.5 ml) was added isopropylsulfonyl chloride (0.22 μL 0.2 mmol) dropwise. After stirring for 18 h, the reaction was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica, 40–50% ethyl acetate/hexanes) to give the title compound 6A-1 as a colorless foam (49 mg).

Workup

  1. customthe reaction was partitioned between ethyl acetate and saturated sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica, 40–50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5c458a1283244533b78268d3193763e1
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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