Bis-(1H-imidazol-2-YL)-methanone → HCID 90337941, compound

HRID 512128Notes

Reaction equation

HRID 512128 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([NH:22][C:23](=[O:28])[C:24]([NH:26][NH2:27])=[O:25])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=2)[CH:7]=1.[C:31](C1NC=CN=1)(C1NC=CN=1)=[O:32]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C@@H:15]([NH:22][C:23]([C:24]3[O:25][C:31](=[O:32])[NH:27][N:26]=3)=[O:28])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86729710HCID 86729710, compound

Product 1

HCID 90337941HCID 90337941, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-ethyl 4-(5′-fluoro-2′-methoxy-[1,1′-biphenyl]-4-yl)-3-(2-hydrazinyl-2-oxoacetamido)butanoate (4.7 g, 11 mmol) in THF (115 mL) was added carbonyl diimidazole (2.4 g, 14 mmol) and the reaction mixture was stirred at room temperature for 24 hours then concentrated to a yellow oil than was purified by silica gel chromatography (40-45% ethyl acetate/hexane) to afford (R)-ethyl 4-(5′-fluoro-2′-methoxy-[1,1′-biphenyl]-4-yl)-3-(5-oxo-4,5-dihydro-1,3,4-oxadiazole-2-carboxamido)butanoate 4.25 g (84%). LCMS Method 1 retention time 1.57 min ES+ M+H(+) 443.8; LCUV Method 2 retention time 7.44 min; 1H NMR (400 MHz, MeOH-d) δ ppm 7.44 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 7.03-7.05 (m, 3H), 4.67 (t, 1H), 4.12 (q, J=7.2 Hz, 2H), 3.76 (s, 3H), 2.96 (d, J=6.8 Hz, 2H), 2.66 (d, J=6.8 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H)

Workup

  1. concentrationthen concentrated to a yellow oil
  2. customthan was purified by silica gel chromatography (40-45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cfd93a68e66d4a229d3b1cf02ae1d745
Source dataset
uspto-grants-2015_08
Patent number
US09102635B2

Reaction notes

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