Ammonia → HCID 66956193, compound

HRID 2066670Notes

Reaction equation

HRID 2066670 reaction equation
[Br:1][C:2]1[N:3]([CH2:10][CH:11]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)[CH2:12][O:13][Si](C(C)(C)C)(C)C)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.Cl.C(=O)=O.CC(C)=O.N>CCO.CO>[Br:1][C:2]1[N:3]([CH2:10][CH:11]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:25][CH:24]=2)[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18522661Acetone cardiceHCID 66955727HCID 66955727, compound

Product 1

HCID 66956193HCID 66956193, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Silyl ether 172 (3.42 g, 6.17 mmol) was treated with a solution of 1% HCl in 95% EtOH (desilylation conditions described by Cunico et al., 1980) (31 mL), and the mixture was stirred at room temperature for 12 h. The resulting solution was cooled (CO2/acetone), neutralised by dropwise addition of 7M NH3 in MeOH (6.6 mL) with stirring, and then concentrated to dryness and the residue was chromatographed on silica gel. Elution with 0-30% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 40-50% EtOAc/petroleum ether gave 3-(2-bromo-4-nitro-1H-imidazol-1-yl)-2-{[4-(trifluoromethoxy)phenoxy]methyl}-1-propanol (174) (2.48 g, 91%) as a white solid: mp (CH2Cl2/pentane) 97-99° C.; 1H NMR (CDCl3) δ 7.88 (s, 1H), 7.17 (br d, J=8.5 Hz, 2H), 6.88 (dt, J=9.1, 3.0 Hz, 2H), 4.34 (dd, J=14.4, 7.4 Hz, 1H), 4.31 (dd, J=14.4, 7.1 Hz, 1H), 4.06 (dd, J=9.6, 5.7 Hz, 1H), 4.03 (dd, J=9.6, 4.8 Hz, 1H), 3.88 (dt, J=10.8, 4.4 Hz, 1H), 3.76 (dt, J=10.8, 4.9 Hz, 1H), 2.54 (m, 1H), 1.72 (t, J=4.4 Hz, 1H); HRFABMS calcd for C14H14BrF3N3O5 m/z [M+H]+ 442.0049, 440.0069. found 442.0053, 440.0063.

Workup

  1. stirringwith stirring
  2. concentrationconcentrated to dryness
  3. customthe residue was chromatographed on silica gel
  4. washElution with 0-30% EtOAc/petroleum ether firstly gave foreruns
  5. washfurther elution with 40-50% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-6c8e10feaf3d4f9387c00727fffbfd38
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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