Ethyl diazoacetate → HCID 86644055, compound

HRID 519780Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][CH: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][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]3[N:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:35]=[C:9]23)[CH2:4][CH2:3]1.[N+](=[CH:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[N-]>C([O-])(=O)C.[Rh+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:12]2[C:13](=[O:14])[N:8]([CH:5]3[CH2:6][CH2:7][CH:2]([O:1][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:3][CH2:4]3)[C:9]3[N:10]([N:33]=[C:34]([C:36]([F:38])([F:39])[F:37])[N:35]=3)[C:11]=2[CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=1)#[N:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4′-{[4-(4-hydroxycyclohexyl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (2.14 g), rhodium(II) acetate (dimer) (88 mg) and toluene (20 mL) was added dropwise ethyl diazoacetate (571 mg) under an argon atmosphere at 80° C., and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)] to give the title compound as a colorless amorphous compound (695 mg, 28%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)]

Sources & evidence

ORD record: ord-54387aa074c34d8095d60d55ccb02882
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115136B2

Reaction notes

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