Toluene → HCID 57786115, compound

HRID 1629006Notes

Reaction equation

HRID 1629006 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][N:10]1[C:14]2[C:15]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])O)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[CH:24]1[C:11]2=[N:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:14]=3[N:10]2[CH2:9][CH2:8][N:7]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86632922HCID 86632922, compound

Product 1

HCID 57786115HCID 57786115, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl(2-{2-[(2,4-dichlorophenyl)(hydroxy)methyl]-7-(diethylamino)-1H-benzimidazol-1-yl}ethyl)carbamate (Reference example 223, 100 mg, 0.197 mmol) and triphenylphosphine (77.5 mg, 0.295 mmol) in tetrahydrofuran (2 mL) was added a solution of diethyl azodicarboxylate in toluene (40%, 0.135 mL, 0.296 mmol) at room temperature. The mixture was stirred at room temperature for 30 min, concentrated in vacuo, and purified by column chromatography on silica gel eluting with a 15-30% ethyl acetate/n-hexane gradient mixture to give a yellow oil (54.8 mg, 0.119 mmol, 60%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography on silica gel eluting with a 15-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-eabd4652c419489ead0498b187630466
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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