Pyridine → HCID 57718399, compound

HRID 1169960Notes

Reaction equation

HRID 1169960 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].N1C=CC=CC=1.[O:22]=[C:23](Cl)[O:24][C:25](Cl)(Cl)Cl.[CH3:30][O:31][C:32]1[C:37]2[O:38][CH2:39][O:40][C:36]=2[CH:35]=[C:34](CO)[CH:33]=1>C(#N)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[N:15]([C:23]([O:24][CH2:25][C:34]2[CH:33]=[C:32]([O:31][CH3:30])[C:37]3[O:38][CH2:39][O:40][C:36]=3[CH:35]=2)=[O:22])[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10426DiphosgeneHCID 602667(7-Methoxy-1,3-benzodioxol-5-yl)methanolHCID 216625422-(1-(2,3-Dimethylphenyl)ethyl)-1H-imidazole

Product 1

HCID 57718399HCID 57718399, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of the compound of Example 1 (180 mg, 0.90 mmol) and pyridine (146 μl, 1.80 mmol) in anhydrous acetonitrile (3 ml), at 0° C. and under nitrogen, was added diphosgene (54 μl, 89 mg, 0.45 mmol). The mixture was allowed to warm to room temperature and stirred for 10 min, before addition of (7-methoxy-1,3-benzodioxol-5-yl)methanol (137 mg, 0.75 mmol) in acetonitrile (1 ml), via syringe. The reaction mixture was stirred at room temperature for 30 min and then filtered.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-c014c8bdd9a04d9281b0dbe5203a23dc
Source dataset
uspto-grants-2010_11
Patent number
US07825149B2

Reaction notes

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