Trifluoromethylsulfonamide → HCID 18315509, compound

HRID 1699616Notes

Reaction equation

HRID 1699616 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:8]=2[CH:21]=1)(O)=[O:2].[F:22][C:23]([F:29])([F:28])[S:24]([NH2:27])(=[O:26])=[O:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[ClH:20].[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:8]2[CH:21]=[C:4]([C:1](=[O:2])[NH:27][S:24]([C:23]([F:29])([F:28])[F:22])(=[O:26])=[O:25])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12]

Participants

5

Reactant 3

HCID 79001TrifluoromethylsulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18315509HCID 18315509, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N′-carbonyldiimidazole (0.647 g) is added all at once to an N,N-dimethylformamide (20 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.600 g) (example 75), and the solution is stirred for one hour at room temperature. Subsequently, an N,N-dimethylformamide (5 ml) solution of trifluoromethanesulfonamide (0.596 g) and diazabicycloundecene (0.609 g) is added, and the solution is stirred for 72 hours at 100° C. The reaction solution is cooled and the solvent is removed through evaporation under reduced pressure. Water and ethyl acetate are added to the residue. While being stirred, 10% hydrochloric acid is added until the aqueous layer became acidic. Precipitated crystals are washed with a mixture solvent of ethanol (25 ml) and methanol (25 ml). The crystals are dried and thus, 1-(2-chlorobenzyl)-2-methyl-6-trifluoromethanesulfonylcarbamoylbenzimidazole hydrochloride (214) (0.420 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.84 (3H, s), 5.82 (2H, s), 7.08 (1H, d, J=7.5 Hz), 7.30 (1H, t), 7.40 (1H, t, J=7.7 Hz), 7.58 (1H, d, J=8.0 Hz), 7.79 (1H, d, J=8.6 Hz), 8.07-8.13 (2H, m).

Workup

  1. stirringthe solution is stirred for 72 hours at 100° C
  2. temperatureThe reaction solution is cooled
  3. customthe solvent is removed through evaporation under reduced pressure
  4. additionWater and ethyl acetate are added to the residue
  5. stirringWhile being stirred
  6. addition10% hydrochloric acid is added until the aqueous layer
  7. customPrecipitated crystals
  8. washare washed with a mixture solvent of ethanol (25 ml) and methanol (25 ml)
  9. customThe crystals are dried

Sources & evidence

ORD record
ord-0f894c03f4c84529a35774512afcd3ea
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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