Methanesulfonyl chloride → HCID 67219167, compound

HRID 1788284Notes

Reaction equation

HRID 1788284 reaction equation
[Cl:1][C:2]1[C:40]([Cl:41])=[CH:39][C:5]2[NH:6][C:7]([O:9][CH:10]([C:19]3([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([C:37]#[N:38])[CH:32]=5)=[CH:27][CH:26]=4)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[N:8][C:4]=2[CH:3]=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:40]([Cl:41])=[CH:39][C:5]2[NH:6][C:7]([O:9][CH:10]([C:19]3([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([C:37]#[N:38])[CH:32]=5)=[CH:27][CH:26]=4)[CH2:24][CH2:23][N:22]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:21][CH2:20]3)[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67218842HCID 67218842, compound

Product 1

HCID 67219167HCID 67219167, compoundYield 128.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.030 g of 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidin-4-yl}-biphenyl-3-carbonitrile (0.05 mmol) 55 in 1 mL of dichloromethane was added methanesulfonyl chloride (0.005 mL, 0.053 mmol, 1.1 eq) and DIEA (0.011 mL, 0.06 mmol, 1.2 eq). The resulting mixture was stirred at room temperature for 16 h, diluted with 5 mL of ethyl acetate, and washed with H2O and saturated brine. The organic extracts were combined and dried over Na2SO4, filtered and concentrated by rotary evaporation to give 0.044 g of 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-1-methanesulfonyl-piperidin-4-yl}-biphenyl-3-carbonitrile as a pale foam. MS (ESI): m/z 684.8/686.8 (M+1/M+3).

Workup

  1. washwashed with H2O and saturated brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-1b2ab63d2f4d41b7b48473b6d268090e
Source dataset
uspto-grants-2009_03
Patent number
US07511146B2

Reaction notes

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