HCID 25152788, compound → HCID 178439223, compound

HRID 2090097Notes

Reaction equation

HRID 2090097 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:35]([CH3:37])[CH3:36])[C:6]2[O:10][C:9]([C:11]3[CH:33]=[CH:32][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][C:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[CH:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:34]=1)#[N:2]>CO.O1CCCC1.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:35]([CH3:37])[CH3:36])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([C:25]5[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:32][CH:33]=3)=[N:8][C:7]=2[CH:34]=1)#[N:2].[C:1]([C:3]1[CH:4]=[C:5]([CH:35]([CH3:37])[CH3:36])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@@H:22]([C:25]5[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:32][CH:33]=3)=[N:8][C:7]=2[CH:34]=1)#[N:2]

Participants

6

Reactant 1

HCID 25152788HCID 25152788, compound

Product 2

HCID 178439223HCID 178439223, compoundYield 46.5%HCID 178439224HCID 178439224, compoundYield 39.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[4-(4-fluorophenyl)cyclohex-3-en-1-yl]methyl}benzamide (30 mg, 0.061 mmol, EXAMPLE 41) in methanol (1 ml) and tetrahydrofuran (1 ml) was added 10% palladium on carbon (10 mg, 0.094 mmol). The mixture was flushed with nitrogen, then flushed with hydrogen and stirred for 6 h under a hydrogen balloon, at which point LC/MS analysis showed no starting material. The mixture was added directly to a 1000-micron plate and then eluted with 1:1 ethyl acetate-hexanes to provide the desired products trans-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[4-(4-fluorophenyl)cyclohexyl]methyl}benzamide (11.9 mg, 0.024 mmol, 39.5% yield) and cis-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[4-(4-fluorophenyl)cyclohexyl]methyl}benzamide (14.0 mg, 0.028 mmol, 46.5% yield).

Workup

  1. customThe mixture was flushed with nitrogen
  2. customflushed with hydrogen
  3. additionThe mixture was added directly to a 1000-micron plate
  4. washeluted with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-3d3dc9c90b104accb5f7a21e8d96d2bb
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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