2-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide → HCID 178509908, compound

HRID 1875085Notes

Reaction equation

HRID 1875085 reaction equation
[N:1]([C:4]1[NH:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Cl:9])[N:8]=1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C>[NH2:1][C:4]1[NH:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Cl:9])[N:8]=1

Participants

4

Reactant 1

HCID 1785099102-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide

Product 1

HCID 178509908HCID 178509908, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Lindlar Catalyst (0.167 g, 0.078 mmol) was added to a suspension of 2-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (0.824 g, 1.569 mmol) in ethyl acetate (30 mL) in a pressure vessel. The vessel was evacuated and flushed with nitrogen, then evacuated and filled with hydrogen (50 psi). The reaction mixture was stirred for 7 h, then filtered through celite. The filtrate was evaporated to dryness and the residue was triturated with ethanol and dried under vacuum to give the title compound (0.350 g, 44%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.95 (br. s., 1H), 7.80 (s, 1H), 7.76 (t, 1H), 7.60 (d, 1H), 7.48 (s, 1H), 7.42 (m, 1H), 7.26 (t, 1H), 5.79 (br. s., 2H), 4.45 (d, 2H). ES MS m/z 498 (M−H).

Workup

  1. customThe vessel was evacuated
  2. customflushed with nitrogen
  3. customevacuated
  4. additionfilled with hydrogen (50 psi)
  5. filtrationfiltered through celite
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was triturated with ethanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-39c2f1a1736b473b8006d54d6f847cc6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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