Trifluoroacetic acid → 4-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]aniline

HRID 969994Notes

Reaction equation

HRID 969994 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)OC(C)(C)C)=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:12][N:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69433847Tert-butyl 4-[2-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]phenylcarbamate

Product 1

HCID 111622684-[2-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrimidin-5-yl]aniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 18B (340 mg, 0.86 mmol) in CH2Cl2 (6 mL) was treated with trifluroacetic acid (Aldrich, 2 mL) at ambient temperature for 30 minutes and concentrated under reduced pressure. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.07) as solid (150 mg, yield, 58%). 1H NMR (300 MHz, MeOH-d4) δ 1.88-2.22 (m, 3H), 2.31-2.45 (m, 1H), 2.56-2.64 (m, 1H), 3.27-3.51 (m, 5H), 3.84-3.96 (m, 1H), 5.36-5.45 (m, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 8.77 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.07) as solid (150 mg, yield, 58%)

Sources & evidence

ORD record
ord-411ad5ed0bfd4de9bb0ad2fb99276d51
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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