Ethyl diazoacetate → HCID 178438773, compound

HRID 2062587Notes

Reaction equation

HRID 2062587 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>[C:23]([C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[C:19]1[S:20][C:16]([CH2:15][C:12]2[C:13](=[O:14])[N:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([O:1][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:3][CH2:4]3)[C:9]3[N:10]([N:32]=[CH:33][N:34]=3)[C:11]=2[CH2:29][CH2:30][CH3:31])=[CH:17][CH:18]=1)#[N:24]

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-2996924f982e4b6f8ea901ddd297b77e
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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