Ethyl diazoacetate → HCID 178438755, compound

HRID 1412447Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:27]2[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:26])[N:11]([C@H:21]2[CH2:24][C@@H:23]([OH:25])[CH2:22]2)[C:12]2[N:13]([N:18]=[CH:19][N:20]=2)[C:14]=1[CH2:15][CH2:16][CH3:17].[N+](=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N-]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O:25][C@H:23]1[CH2:22][C@@H:21]([N:11]2[C:10](=[O:26])[C:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]#[N:34])=[CH:3][C:2]=3[F:1])=[C:14]([CH2:15][CH2:16][CH3:17])[N:13]3[N:18]=[CH:19][N:20]=[C:12]23)[CH2:24]1)[CH3:42]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3′-fluoro-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 (0.67 g), rhodium(II) acetate (dimer) (0.0066 g) and toluene (10 mL) was heated to 80° C. under an argon atmosphere, a solution of ethyl diazoacetate (1.5 g) in toluene (10 mL) was added dropwise, and the mixture was stirred at 80° C. for 10 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.29 g, 37%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f4f59e0ba6024315b0c48242b5ea8e63
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921379B2

Reaction notes

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