3-(Pyrrolidin-2-yl)pyridine → HCID 87464498, compound

HRID 2245379Notes

Reaction equation

HRID 2245379 reaction equation
[I-].C[N+]1C=CN([C:8](=[O:30])/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[O:22][C:17]=3[CH:16]=2)C=1.C(N(CC)C(C)C)(C)C.[NH:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1>C(#N)C>[CH3:29][C:12]1[S:11]/[C:10](=[N:9]\[C:8]([N:40]2[CH2:44][CH2:43][CH2:42][CH:41]2[C:45]2[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=2)=[O:30])/[N:14]([C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:25])([F:26])[C:21]([F:23])([F:24])[O:22][C:17]=3[CH:16]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 4123-(Pyrrolidin-2-yl)pyridineHCID 81531DiisopropylethylamineHCID 87462668HCID 87462668, compound

Product 1

HCID 87464498HCID 87464498, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide core (Example 81A, 0.88 mL of 0.16 M in acetonitrile, 80 mg, 0.1 mmol) was added to a 20 mL vial, followed by N,N-diisopropylethylamine (0.88 mL of 0.2 M in acetonitrile, 24 mg, 0.13 mmol). 3-(Pyrrolidin-2-yl)pyridine (0.79 mL of 0.2 M in acetonitrile, 0.11 mmol) was added last. The resulting mixture was shaken at room temperature overnight. It was then concentrated in vacuo, and the residue was taken up in 1:1 MeOH/DMSO and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method) to give the titled compound. 1H NMR (300 MHz, DMSO-d6/D2O) δ ppm 1.74-1.93 (3H) 2.12-2.21 (3H) 2.33-2.44 (1H) 3.50-3.68 (2H) 4.95-5.07 (1H) 6.91-7.06 (1H) 7.21-7.59 (3H) 7.70-7.91 (1H) 8.33-8.42 (1H) 8.44-8.52 (1H); MS (ESI+) m/z 495 (M+H)+.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. custompurified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method)

Sources & evidence

ORD record
ord-5d3e5110d104457591b1cfa0226728f9
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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