Hydrochloric Acid → 4-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-2-nitro-phenylamine

HRID 970015Notes

Reaction equation

HRID 970015 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[N:16][C:17]([O:20][C@@H:21]3[CH:26]4[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]4)[CH2:22]3)=[CH:18][CH:19]=2)=[CH:10][C:9]=1[N+:29]([O-:31])=[O:30])(C)(C)C.Cl>CCO>[N:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:17]1[N:16]=[N:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([N+:29]([O-:31])=[O:30])[CH:10]=3)=[CH:19][CH:18]=1)[CH2:22]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67070172{4-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-2-nitro-phenyl}-carbamic Acid tert-butyl Ester

Product 1

HCID 114165594-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 34C (350 mg, 0.79 mmol) was treated with HCl (Aldrich, 4 M in dioxane, 2 mL, 8 mmol) in EtOH (5 mL) at ambient temperature for 1 h. The mixture was concentrated and the title compound was purified by chromatography (SiO2, EtOAc: MeOH (v. 2% NH3.H2O), 50:50, Rf. 0.1) as white solid (250 mg, 93%). 1H NMR (300 MHz, MeOH-D4) δ 1.54-1.66 (m, 1 H), 1.72-2.02 (m, 2 H), 2.07-2.24 (m, 1 H), 2.35-2.57 (m, 1 H), 2.79-3.18 (m, 5 H), 3.48-3.69 (m, 1 H), 5.27-5.47 (m, 1 H), 7.10 (d, J=8.8 Hz, 1 H), 7.22 (d, J=9.5 Hz, 1 H), 7.66 (s, 1 H), 7.98 (d, J=9.2 Hz, 1 H), 8.08 (dd, J=9.0, 2.2 Hz, 1 H), 8.68 (d, J=2.4 Hz, 1 H) ppm. MS (DCl/NH3): 342 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe title compound was purified by chromatography (SiO2, EtOAc: MeOH (v. 2% NH3.H2O), 50:50, Rf. 0.1) as white solid (250 mg, 93%)

Sources & evidence

ORD record
ord-b357718bd36a44adab79113f0a274a13
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

Loading…