Hydroxylamine → HCID 22380350, compound

HRID 1988767Notes

Reaction equation

HRID 1988767 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=O)=[N:8][C:4]=2[CH:3]=1.[CH3:24]N(C(N(C)C)N(C)C)C.[NH2:34][OH:35]>CCO>[Br:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([CH2:20][CH3:21])[C:7]([CH2:9][C:10]3[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=4)=[N:34][O:35][CH:24]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 22379891HCID 22379891, compound

Product 1

HCID 22380350HCID 22380350, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(5-Bromo-1-ethyl-1H-benzoimidazol-2-yl)-1-(3-fluoro-phenyl)-propan-1-one (0.1 g, 0.27 mmol) and tris(dimethylamino)methane (0.077 g, 0.54 mmol) is heated at 60° C. in a sealed tube for 6 hours. The volatile material is removed in vacuo. To the residue is added EtOH (5 mL) and hydroxylamine (1.1 mmol). The mixture is heated at 120° C. for 2 hours. The solvent is removed. To the residue is added NaHCO3 (aq.) (10 mL) and DCM (30 mL). The organic layer is separated and the aqueous layer is extracted with DCM (2×15 mL). The combined organic layers are dried and the solvent removed. The crude is purified by PTLC (ethyl acetate/Hexanes 1:1) to give 5-Bromo-1-ethyl-2-[3-(3-fluoro-phenyl)-isoxazol-4-ylmethyl]-1H-benzoimidazole as a solid. 1H NMR (CDCl3) δ 8.40 (s, 1H), 7.88 (s, 1H), 7.31-7.52 (m, 4H), 7.18-7.22 (m, 2H), 4.14 (s, 2H), 4.04 (q, 2H), 1.18 (t, 3H).

Workup

  1. customThe volatile material is removed in vacuo
  2. temperatureThe mixture is heated at 120° C. for 2 hours
  3. customThe solvent is removed
  4. additionTo the residue is added NaHCO3 (aq.) (10 mL) and DCM (30 mL)
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with DCM (2×15 mL)
  7. customThe combined organic layers are dried
  8. customthe solvent removed
  9. customThe crude is purified by PTLC (ethyl acetate/Hexanes 1:1)

Sources & evidence

ORD record
ord-6909e488e80d4165bc8ebb6a56fbe73a
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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