Dichloromethane → N-(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-N-propylsulfamide

HRID 271308Notes

Reaction equation

HRID 271308 reaction equation
[Cl:1][C:2]1[CH2:3][CH:4]2[CH:25]([NH2:26])[CH:7]([CH2:8][C:9]=1/[CH:10]=[CH:11]/[C:12]1[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[N:14]([CH3:24])[N:13]=1)[CH2:6][CH2:5]2.C(N([CH2:32][CH3:33])CC)C.C([NH:37][S:38](Cl)(=[O:40])=[O:39])CC.[CH2:42](Cl)Cl>O>[Cl:1][C:2]1[CH2:3][CH:4]2[CH:25]([N:26]([CH2:42][CH2:32][CH3:33])[S:38]([NH2:37])(=[O:40])=[O:39])[CH:7]([CH2:8][C:9]=1/[CH:10]=[CH:11]/[C:12]1[CH:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[N:14]([CH3:24])[N:13]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13398949N-propylsulfamoyl chlorideHCID 69306506(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)amine

Product 1

HCID 69306475N-(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-N-propylsulfamideYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product from Step 6 (100 mg, 0.27 mmol), triethylamine (110 mg, 1.1 mmol) and propylsulfamoyl chloride (170 mg, 1.1 mmol) in DCM (5 ml) was stirred at ambient temperature for 18 hrs. The reaction mixture was diluted with water (20 ml) and extracted with ethyl acetate (3×20 ml). The organic extracts were washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate: hexane (1:4) to afford N-(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-N-propylsulfamide (98 mg, 74%). δH (400 MHz, CDCl3) 0.98 (3H, t, J 7.5), 1.42-1.48 (1H, m), 1.54-1.62 (4H, m), 1.82-1.90 (2H, m), 2.38-2.62 (3H, m), 2.68-2.76 (2H, m), 2.98-3.08 (3H, m), 3.72-3.77 (1H, m), 3.82 (2H, s), 4.13-4.18 (1H, m), 4.33 (1H, d, J 9.0), 6.48 (1H, s), 6.64 (1H, d, J 16.5), 7.12-7.18 (2H, m), 7.37-7.43 (2H, m), 7.45 (1H, d, J 16.5).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe organic extracts were washed with brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate: hexane (1:4)

Sources & evidence

ORD record
ord-6bf65542364b49848b57f2a5c70c450d
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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