Fusaric Acid → HCID 45381411, compound

HRID 2088313Notes

Reaction equation

HRID 2088313 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH2:10][C@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1.[CH3:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29](O)=[O:30])=[N:27][CH:28]=1.[I-].ClC1C=CC=C[N+]=1C>O.C(#N)C>[CH2:22]([C:23]1[CH:24]=[CH:25][C:26]([C:29]([NH:10][C@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:30])=[N:27][CH:28]=1)[CH2:21][CH2:20][CH3:19]

Participants

7

Reactant 4

HCID 3442Fusaric AcidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 45381411HCID 45381411, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1.5 ml of Acetonitrile and Triethylamine (700 uL, 5.0 mmol) was added to a flask charged with (S)-(−)-3-Aminoquinuclidine dihydrochloride (199 mg, 1.0 mmol) and Fusaric acid (197 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methylpyridinium iodide (383 mg, 1.5 mmol) at room temperature. After stirring overnight, about 2 ml of water was added to reaction mixture to resolve a clear solution that was subsequently injected into a Preparative HPLC instrument for purification. Desired fractions were combined and concentrated under vacuum. (S)-5-butyl-N-(quinuclidin-3-yl)pyridine-2-carboxamide (273 mg, 95% yield) was isolated as clear brown colored oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 8.52 (d, J=1.8 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.84 (dd, J=8.0 Hz, 1H), 4.50 (m, 1H), 3.82 (ddd, J=10.0, 3.0, 2.6 Hz, 1H), 3.49 (m, 1H), 3.37 (m, 3H), 2.76 (t, J=7.8 Hz, 2H), 2.38 (m, J=3.1 Hz, 1H), 2.26 (m, 1H), 2.12 (td, J=8.0, 3.1 Hz 2H), 1.96 (m, 1H), 1.68 (m, J=7.7 Hz, 2H), 1.40 (m, J=4.5 Hz, 2H), 0.97 (t, J=7.4 Hz, 3H). LCMS (ESI): m/z 288.1 (M+H [C17H25N3O]=288.20).

Workup

  1. customwas subsequently injected into a Preparative HPLC instrument for purification
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c6cf4b1b034448fa869c0edb00ac5a17
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

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