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Dimethylamine tetrahydrofuran → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

HRID 2239297
Notes
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Reaction equation

HRID 2239297 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[CH:21]=1.[O:30]1[CH2:34]CCC1.[CH3:35][NH:36][CH3:37]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:35][N:36]([CH3:37])[C:34]([C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)(=[O:13])=[O:12])[C:6]=2[CH:21]=1)=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 67219535HCID 67219535, compound

Product 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamideYield 42%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6-bromo-2-methyl-1-[(4-methylphenyl)sulfonyl]-4-[(phenylmethyl)oxy]-1H-benzimidazole (53.0 g, 112 mmol, STEP 2) and tetrakis(triphenylphosphine)palladium(0) (25.9 g, 22.4 mmol) in 2M dimethylamine tetrahydrofuran solution (580 mL) was stirred at 65° C. under carbon mono-oxide gas (1 atmosphere) for 32 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate (600 mL). The organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL), dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3) to afford the title compound as a white solid (21.8 g, 42%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3)

Sources & evidence

ORD record
ord-6d5cb90a823b4ba69bc72c8abc6d4df6
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723321B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes