Trifluoroacetic acid → 3-{4-[(5-bromopyrimidin-2-yl)oxy]phenoxy}quinuclidine Trifluroacetate

HRID 1294665Notes

Reaction equation

HRID 1294665 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:23]=[CH:22][C:12]([O:13][CH:14]3[CH:19]4[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]4)[CH2:15]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>C(OCC)(=O)C>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH:14]3[CH:19]4[CH2:18][CH2:17][N:16]([CH2:21][CH2:20]4)[CH2:15]3)=[CH:22][CH:23]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 112573713-{4-[(5-Bromopyrimidin-2-yl)oxy]phenoxy}quinuclidine

Product 1

HCID 695202013-{4-[(5-bromopyrimidin-2-yl)oxy]phenoxy}quinuclidine Trifluroacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 16A (100 mg, 0.26 mmol) in ethyl acetate (4 mL) was treated with trifluroacetic acid (113 mg, 1 mmol). The title compound was obtained as solid (100 mg, yield, 64%). 1H NMR (MeOH-d4, 300 MHz) δ 1.85–2.16 (m, 3H), 2.25–2.46 (m, 1H), 2.56 (m, 1H), 3.30–3.53 (m, 5H), 3.80 (m, 1H), 4.95 (m, 1H), 7.04 (dt, J=9.1, 2.4 Hz, 2H), 7.14 (dt, J=9.1, 2.3 Hz, 2H), 8.60 (s, 2H) ppm. MS (DCl/NH3) m/z. m/z 376 (M+H)+, 378 (M+H)+. Anal. Calculated for C17H18BrN3O2.2.0CF3CO2H.2.0H2O: C, 39.39; H, 3.78; N, 6.56. Found: C, 39.19; H, 3.78; N, 6.83.

Sources & evidence

ORD record
ord-99d336c6a5dc4a6bb4e79cd72e30bc93
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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