Toluene → HCID 57786213, compound

HRID 1399350Notes

Reaction equation

HRID 1399350 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][OH:18])[C:13]2[C:19]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:20][C:21]([F:23])=[CH:22][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[C:13](=[C:19]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH:20]=[C:21]([F:23])[CH:22]=3)[N:14]2[CH2:15][CH2:16][CH2:17][O:18]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68763137HCID 68763137, compound

Product 1

HCID 57786213HCID 57786213, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-{2-[(2,4-dichlorophenyl)(hydroxy)methyl]-7-(diethylamino)-5-fluoro-1H-benzimidazol-1-yl}propan-1-ol (Reference example 212, 44.0 mg, 0.100 mmol) and triphenylphosphine (26.2 mg, 0.100 mmol) in tetrahydrofuran (2 mL) was added a solution of diethyl azodicarboxylate in toluene (40%, 68.3 μL, 0.150 mmol) at room temperature. After 90 h, the reaction mixture was concentrated in vacuo, and purified by column chromatography on NH silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture to give colorless oil (10.1 mg, 0.0238 mmol, 24%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on NH silica gel eluting with a 0-20% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-1e24102668ef4302ad3743527a2f706e
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…