Toluene → HCID 57786317, compound

HRID 1629009Notes

Reaction equation

[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2[C:16]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])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:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[CH:25]1[C:12]2=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:15]=3[N:11]2[CH2:10][CH2:9][CH2:8][N:7]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:35]

Participants

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

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

Sources & evidence

ORD record: ord-cd36bd6e7a5b47649db3b432a23c789e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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