Fumaric Acid → HCID 66629517, compound

HRID 617287Notes

Reaction equation

HRID 617287 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19]>CO>[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 97941413-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridine

Product 1

HCID 66629517HCID 66629517, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound of step 4a was dissolved in anhydrous MeOH and brought to 0° C. with stirring. Fumaric acid was dissolved in MeOH with sonication and added dropwise to the solution containing amine. The mixture was warmed to room temperature with stirring. After 30 minutes the solvent was evaporated in vacuo and the remaining solid was vacuum filtered. The solid was then recrystallized with MeOH/Et2O to give the desired product as a white powder (21% yield). m.p.=124-125° C. [α]25D =-3.9° (c=1, MeOH). MS (DCI/NH3) m/e 193 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.43 (br s, 1H, 8.33 (d, J=4.5 Hz, 1H), 7.88-7.84 (m, 1H), 7.3 (dd, J=8.82, 5.15 Hz, 1H), 6.58 (s, 2H), 4.59 (dd, J=11, 3 Hz, 1H), 4.42 (dd, J=11, 5.98 Hz, 1H), 4.05-3.9 (m, 1H), 3.82-3.74 (m, 1H, 3.343.22 (m, 1H), 3.05 (s, 3H), 2.47-2.37 (m, 1H), 2.30-2.06 (m, 3H). Analysis calculated for C11H16N2O.C4H4O4 : C, 58.43; H, 6.54; N, 9.09; Found: C, 58.32; H, 6.67; N, 8.99.

Workup

  1. custombrought to 0° C.
  2. additionadded dropwise to the solution
  3. stirringwith stirring
  4. customAfter 30 minutes the solvent was evaporated in vacuo
  5. filtrationfiltered
  6. customThe solid was then recrystallized with MeOH/Et2O

Sources & evidence

ORD record
ord-cafad93810f2457a85feea891b992c19
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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