Water → HCID 178438759, compound

HRID 1688819Notes

Reaction equation

HRID 1688819 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][C:17]=3[O:30][CH3:31])=[C:11]([CH2:32][CH2:33][CH3:34])[N:10]3[N:35]=[CH:36][CH:37]=[C:9]23)[CH2:4][CH2:3]1.[N+](=[CH:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[N-].C(OCC)(=O)C.O>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:12]2[C:13](=[O:14])[N:8]([C@H:5]3[CH2:4][CH2:3][C@H:2]([O:1][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:7][CH2:6]3)[C:9]3[N:10]([N:35]=[CH:36][CH:37]=3)[C:11]=2[CH2:32][CH2:33][CH3:34])=[C:17]([O:30][CH3:31])[CH:18]=1)#[N:29]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12192Ethyl diazoacetateHCID 178438757HCID 178438757, compound

Product 1

HCID 178438759HCID 178438759, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4′-{[4-(trans-4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-3′-methoxybiphenyl-2-carbonitrile (0.93 g) and rhodium acetate (dimer, 0.020 g) in methylene chloride (10 mL) was added dropwise ethyl diazoacetate (0.86 mL), and the mixture was stirred for 3 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.52 g, 47%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22f4655ec4084e8cb1604e2f015ec5cb
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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