Potassium Carbonate → HCID 57935976, compound

HRID 1434593Notes

Reaction equation

HRID 1434593 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:12][S:13]([C:16]1[CH:30]=[CH:29][C:19]2[N:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:21]=[N:22][C:18]=2[CH:17]=1)(=[O:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][S:13]([C:16]1[CH:30]=[CH:29][C:19]2[N:20]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][C:4]([C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:5])[CH2:27][CH2:28]3)[CH:21]=[N:22][C:18]=2[CH:17]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 702953-ChloropropiophenoneHCID 58998518HCID 58998518, compound

Product 1

HCID 57935976HCID 57935976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloropropiophenone (860 mg) was added to a mixture of 5-(methylsulfonyl)-1-piperidin-4-yl-1H-benzimidazole (1.395 g) and potassium carbonate (1.38 g) in DMF (30 ml) and stirred for 2 days. The reaction mixture was evaporated to dryness and the residue was dissolved in dichloromethane (20 ml), washed with water (15 ml) and brine (15 ml), dried and evaporated to dryness to give the title compound, yield 2.07 g, M+H 412, NMR (CDCl3) 2.2 (m, 4H) 2.3-2.4 (m, 2H) 2.9 (m, 2H) 3.1 (s, 3H) 3.2-3.3 (m, 4H) 4.3 (m, 1H) 7.5 (m, 2H) 7.6 (m, 2H) 7.9 (m, 2H) 8.0 (m, 1H) 8.2 (s, 1H) 8.4 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  3. washwashed with water (15 ml) and brine (15 ml)
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7fb6528ba5244589b175c6f75cd62349
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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