Toluene → HCID 57786317, compound

HRID 1399361Notes

Reaction equation

HRID 1399361 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9](O)[C:10]1[N:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]2[C:26]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:27][CH:28]=[CH:29][C:12]=2[N:11]=1.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:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]2=[N:11][C:12]3[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:13]=3[N:14]2[CH2:15][CH2:16][CH2:17][N:18]1[C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86632927HCID 86632927, compound

Product 1

HCID 57786317HCID 57786317, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl (3-{2-[(2,4-dichlorophenyl)(hydroxy)methyl]-7-(diethylamino)-1H-benzimidazol-1-yl}propyl)carbamate (Reference example 228, 500 mg, 0.959 mmol) and triphenylphosphine (377 mg, 1.44 mmol) in tetrahydrofuran (30 mL) was added a solution of diethyl azodicarboxylate in toluene (40%, 0.655 mL, 1.44 mmol) at 0° C. The mixture was stirred at 0° C. for 2 h, concentrated in vacuo, and purified by column chromatography on silica gel eluting with a 10-20% ethyl acetate/n-hexane gradient mixture to give a colorless amorphous solid (138 mg, 0.274 mmol, 29%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography on silica gel eluting with a 10-20% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-fc8ec52ac64a4cbf9158852ac1daa31d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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