Ethyl diazoacetate → HCID 178438773, compound

HRID 1412364Notes

Reaction equation

HRID 1412364 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[S:20][C:19]([C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]#[N:24])=[CH:18][CH:17]=3)=[C:11]([CH2:29][CH2:30][CH3:31])[N:10]3[N:32]=[CH:33][N:34]=[C:9]23)[CH2:4][CH2:3]1.[N+](=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N-]>C([O-])(=O)C.[Rh+].C1(C)C=CC=CC=1>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O: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[S:20][C:19]([C:21]4[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=4[C:23]#[N:24])=[CH:18][CH:17]=3)=[C:11]([CH2:29][CH2:30][CH3:31])[N:10]3[N:32]=[CH:33][N:34]=[C:9]23)[CH2:4][CH2:3]1)[CH3:42]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 178438771HCID 178438771, compound

Product 1

HCID 178438773HCID 178438773, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178476747HCID 178476747, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 2-(5-{[4-(trans-4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}thiophen-2-yl)benzonitrile (0.4 g), rhodium(I) acetate (0.0019 g) and toluene (10 mL) was added dropwise ethyl diazoacetate (0.46 mL) at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography to give the title compound as a colorless solid (0.25 g, 53%).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f7fa6886c4f74473abbbe8b828f0a8ae
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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