Ethyl diazoacetate → HCID 178438699, compound

HRID 1412359Notes

Reaction equation

HRID 1412359 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([N:6]2[C:11](=[O:12])[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[C:9]([CH2:28][CH2:29][CH3:30])[N:8]3[N:31]=[CH:32][N:33]=[C:7]23)[CH2:3]1.[N+](=[CH:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N-]>C([O-])(=O)C.[Rh+].C1(C)C=CC=CC=1>[CH2:40]([O:39][C:37](=[O:38])[CH2:36][O:1][C@H:2]1[CH2:5][C@@H:4]([N:6]2[C:11](=[O:12])[C:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]#[N:27])=[CH:18][CH:19]=3)=[C:9]([CH2:28][CH2:29][CH3:30])[N:8]3[N:31]=[CH:32][N:33]=[C:7]23)[CH2:3]1)[CH3:41]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 178438694HCID 178438694, compound

Product 1

HCID 178438699HCID 178438699, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 178476747HCID 178476747, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 4′-{[4-(cis-3-hydroxycyclobutyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.3 g), rhodium(I) acetate (0.003 g) and toluene (20 mL) was added dropwise ethyl diazoacetate (0.66 mL) at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to give the title compound as a colorless solid (0.2 g, 57%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c16393c539d4798a0036ae70f59c7d1
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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