4-Cyanobenzoyl chloride → HCID 67242813, compound

HRID 2422112Notes

Reaction equation

HRID 2422112 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:12]([N:16]1[C:20](=[O:21])[C:19]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[C:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:17]1(=[O:36])=[O:35])([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([N:16]1[C:20](=[O:21])[C:19]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:7]([C:6]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[O:8])[CH2:25][CH2:24]2)=[C:18]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[S:17]1(=[O:36])=[O:35])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 67241221HCID 67241221, compound

Product 1

HCID 67242813HCID 67242813, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described for Example 105 from 4-cyanobenzoyl chloride and 2-tert-butyl-5-phenyl-4-(piperidin-4-ylamino)isothiazol-3(2H)-one 1,1-dioxide (Example 75) using DMF as solvent. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (Horizons Biotage) using 50% EtOAc in petroleum ether 40-60° C. as eluent. The product containing fractions were evaporated, dissolved in DCM, washed through a cation exchange column and evaporated to give the title compound (0.015 g, 11%). 1H NMR (500 MHz CDCl3): δ 7.70 (d, 1H), 7.55-7.50 (m, 2H), 7.49-7.40 (m, 5H), 5.21 (d, 1H), 4.52-4.40 (m, 1H), 3.50-3.36 (m, 1H), 3.24-3.14 (m, 2H), 2.62-2.44 (m, 2H), 1.92-1.78 (m, 1H), 1.74 (s, 9H), 1.67-1.54 (m, 2H), 1.48-1.16 (m, 2H); 13C NMR (125 MHz CDCl3): δ 168.5, 159.7, 140.1, 133.9, 132.7, 131.8, 130.3, 129.0, 127.7, 125.2, 118.2, 113.9, 107.9, 61.9, 50.1, 46.0, 40.9, 32.9, 32.1, 27.8; M+H+ 493.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by silica gel column chromatography (Horizons Biotage)
  4. custom50% EtOAc in petroleum ether 40-60° C.
  5. additionThe product containing fractions
  6. customwere evaporated
  7. dissolutiondissolved in DCM
  8. washwashed through a cation exchange column
  9. customevaporated

Sources & evidence

ORD record
ord-698d86c944844779b07a36773df2241c
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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