Fumaric Acid → HCID 68574582, compound

HRID 2111897Notes

Reaction equation

HRID 2111897 reaction equation
[CH2:1]([N:5]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH2:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1)[CH:2]([CH3:4])[CH3:3].[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22]>C(OCC)C.ClCCl.CO>[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22].[CH3:3][CH:2]([CH3:4])[CH2:1][N:5]([CH2:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1)[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1

Participants

6

Reactant 2

HCID 444972Fumaric AcidHCID 57640346HCID 57640346, compound

Product 1

HCID 68574582HCID 68574582, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Isobutyl-(piperidin-4-yl)-[(thiazol-4-yl)methyl]-amine (380 mg, 1.50 mmol, 1 eq.) is dissolved in a 1:1 mixture of diethyl ether and dichloromethane. Fumaric acid (191.5 mg, 1.65 mmol, 1.1 eq.) is dissolved in hot anhydrous methanol (1 ml) and then added to the solution of free base. Precipitation occurred upon cooling at 0° C. for 3 days. The precipitate is filtered, rinsed with ether, and dried in a vacuum oven (40° C.) overnight to give the title compound (416 mg, 75%). m/z=254 (M+1); 1H NMR (CD3OD): δ=8.94 (1H, d), 7.44-7.43 (1H, m), 6.68 (2H, s), 3.88 (2H, s), 3.43 (2H, brd), 2.99-2.85 (3H, m) 2.33 (2H, d), 2.04 (2H, brd), 1.83-1.63 (3H, m), 0.87 (6H, d).

Workup

  1. additionadded to the solution of free base
  2. customPrecipitation
  3. filtrationThe precipitate is filtered
  4. washrinsed with ether
  5. customdried in a vacuum oven (40° C.) overnight

Sources & evidence

ORD record
ord-e55ea10d7b8146c6af4ce929b5553011
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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