Water → HCID 21876485, compound

HRID 724194Notes

Reaction equation

HRID 724194 reaction equation
[Cl:1][C:2]1[C:3]([C:43]([F:46])([F:45])[F:44])=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])[N:7]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH:28][C:29]([NH:31][S:32]([C:35]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=4)(=[O:34])=[O:33])=[O:30])=[CH:22][CH:21]=3)[C:6]=2[CH:42]=1.FC(F)(F)C(O)=O.O>C(Cl)Cl>[NH2:12][CH:10]([C:8]1[N:7]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH:28][C:29]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])=[O:30])=[CH:22][CH:21]=2)[C:6]2[CH:42]=[C:2]([Cl:1])[C:3]([C:43]([F:45])([F:44])[F:46])=[CH:4][C:5]=2[N:9]=1)[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 21875590HCID 21875590, compound

Product 1

HCID 21876485HCID 21876485, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl 1-[6-chloro-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-5-(trifluoromethyl)-1H-benzimidazol-2-yl]ethylcarbamate (step 2, 190 mg, 0.28 mmol) in CH2Cl2 (2 ml) was added trifluoroacetic acid (1 ml) and stirred at room temperature for 2 h. The mixture was added water (10 ml) and extracted with CH2Cl2 (20 ml). The organic layer was washed with brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with CH2Cl2/MeOH (10:1/5:1) to afford 160 mg (99%) of the title compound as white solids.

Workup

  1. extractionextracted with CH2Cl2 (20 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with CH2Cl2/MeOH (10:1/5:1)

Sources & evidence

ORD record
ord-10e771b71bfa4b6bbfa9f465cbd99a47
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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