HCID 178418361, compound → HCID 178511391, compound

HRID 658116Notes

Reaction equation

HRID 658116 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[CH:8]=[C:9]([C:13](=[O:34])[C:14](=[C:25]2[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[NH:26]2)[C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)=[O:16])[CH:10]=[CH:11][CH:12]=1)[OH:6])=[N+]=[N-].[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:1][CH2:4][CH:5]([C:7]1[CH:8]=[C:9]([C:13](=[O:34])[C:14](=[C:25]2[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[NH:26]2)[C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)=[O:16])[CH:10]=[CH:11][CH:12]=1)[OH:6]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178514600HCID 178514600, compound

Product 1

HCID 178511391HCID 178511391, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 568 mg portion of 1-[3-(2-azido-1-hydroxyethyl)phenyl]-3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)propane-1,3-dione and 120 mg of 10% palladium-carbon were added to 50 ml of ethyl acetate and stirred at room temperature for 8.5 hours under ordinary pressure and in an atmosphere of hydrogen. This was filtered through celite, concentrated, mixed with diethyl ether and then extracted with water. By concentrating the water layer, 250 mg (47%) of 1-[3-(2-amino-1-hydroxyethyl)phenyl]-3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)propane-1,3-dione (Example 14-1) was obtained as a yellow solid. FA: 436

Workup

  1. filtrationThis was filtered through celite,
  2. concentrationconcentrated
  3. additionmixed with diethyl ether
  4. extractionextracted with water
  5. concentrationBy concentrating the water layer

Sources & evidence

ORD record
ord-71543b5ee3954c8c817252f2b90dd122
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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