Hydrochloric Acid → 4-{2-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyrimidin-5-yl}-2-nitro-phenylamine

HRID 970018Notes

Reaction equation

HRID 970018 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH: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)=[N:18][CH:19]=2)=[CH:10][C:9]=1[N+:29]([O-:31])=[O:30])(C)(C)C.Cl>CCO>[N:23]12[CH2:28][CH2:27][CH:26]([CH2:25][CH2:24]1)[C@@H:21]([O:20][C:17]1[N:16]=[CH: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][N:18]=1)[CH2:22]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69435520{4-{2-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyrimidin-5-yl}-2-nitro-phenyl}-carbamic Acid tert-butyl Ester

Product 1

HCID 117393464-{2-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyrimidin-5-yl}-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 36A (100 mg, 0.23 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 (50 mg, 64%). 1H NMR (500 MHz, MeOH-D4) δ 1.47-1.64 (m, 1 H), 1.65-1.78 (m, 1 H), 1.78-1.91 (m, 1 H), 1.96-2.16 (m, 1 H), 2.15-2.38 (m, 1 H), 2.73-3.05 (m, 5 H), 3.35-3.47 (m, 1 H), 4.96-5.28 (m, 1 H), 7.10 (d, J=8.8 Hz, 1 H), 7.68 (dd, J=8.8, 2.1 Hz, 1 H), 8.32 (d, J=2.1 Hz, 1 H), 8.79 (s, 2 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 (50 mg, 64%)

Sources & evidence

ORD record
ord-7088f1c4d2a34794971c414fe19cf3fd
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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