5-(2-Pyridyl)thiophene-2-sulfonyl chloride → N-{2-[4-(3,4-difluorophenoxy)-1-piperidinyl]ethyl}-5-(2-pyridinyl)-2-thiophenesulfonamide

HRID 1394047Notes

Reaction equation

HRID 1394047 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:29][C:28]([S:30](Cl)(=[O:32])=[O:31])=[CH:27][CH:26]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][S:30]([C:28]2[S:29][C:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=3)=[CH:26][CH:27]=2)(=[O:31])=[O:32])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 693106352-[4-(3,4-Difluorophenoxy)-1-piperidinyl]ethylamine

Product 1

HCID 69314667N-{2-[4-(3,4-difluorophenoxy)-1-piperidinyl]ethyl}-5-(2-pyridinyl)-2-thiophenesulfonamideYield 7.6%

Procedure

To a solution of 5-pyridin-2-yl-thiophene-2-sulfonyl chloride (0.213 g) [in CH2Cl2 (10 ml)] was added a solution of the product of Example 4, Step (b) (0.210 g) [in CH2Cl2 (5 ml) and pyridine (0.066 ml)]. The reaction was left to stir for 12 hrs. The reaction mixture was washed with saturated aqueous NaCl solution and the organics separated and dried and then filtered. The solvents were evaporated and the product purified by using reverse phase HPLC {with a gradient eluent system [25% MeCN/NH4OAcaq (0.1%) to 95% MeCN//NH4OAcaq (0.1%)]} give the title compound as a solid (0.03 g).

Workup

  1. waitThe reaction was left
  2. washThe reaction mixture was washed with saturated aqueous NaCl solution
  3. customthe organics separated
  4. customdried
  5. filtrationfiltered
  6. customThe solvents were evaporated
  7. customthe product purified

Sources & evidence

ORD record
ord-1e23e502866149efbefe7adb5835ee6a
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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