Fumaric Acid → 173334-58-2

HRID 2172656Notes

Reaction equation

HRID 2172656 reaction equation
[CH3:1][CH:2]([C@H:4]([CH2:20][C@H:21]([NH2:39])[C@@H:22]([OH:38])[CH2:23][C@H:24]([C:28]([NH:30][CH2:31][C:32]([C:35]([NH2:37])=[O:36])([CH3:34])[CH3:33])=[O:29])[CH:25]([CH3:27])[CH3:26])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=1)[CH3:3].[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44]>C(O)C.C(#N)C>[CH3:3][CH:2]([C@H:4]([CH2:20][C@H:21]([NH2:39])[C@@H:22]([OH:38])[CH2:23][C@H:24]([C:28]([NH:30][CH2:31][C:32]([C:35]([NH2:37])=[O:36])([CH3:33])[CH3:34])=[O:29])[CH:25]([CH3:26])[CH3:27])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=1)[CH3:1].[CH3:3][CH:2]([C@H:4]([CH2:20][C@H:21]([NH2:39])[C@@H:22]([OH:38])[CH2:23][C@H:24]([C:28]([NH:30][CH2:31][C:32]([C:35]([NH2:37])=[O:36])([CH3:33])[CH3:34])=[O:29])[CH:25]([CH3:26])[CH3:27])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=1)[CH3:1].[CH:41](/[C:40]([OH:47])=[O:46])=[CH:42]\[C:43]([OH:45])=[O:44]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 5493444Aliskiren

Product 1

HCID 6918427173334-58-2Yield 54%

Reagents, catalysts & solvents 1

HCID 21984225Acetonitrile ethanolSolvent2×

Conditions

Temperature
52.5 °C

Procedure

Aliskiren i.e. compound of Formula X (1.5 g, 0.003 mol) and fumaric acid (0.15 g, 0.0013 mol) were dissolved in 5% ethanol/acetonitrile (7.5 mL) and heated to 50-55° C. for 15 min. The reaction mixture was allowed to cool slowly to room temperature and stirred for further 12 h. The slurry formed was diluted with 5% ethanol/acetonitrile (7.5 mL) and filtered under nitrogen. The solid was suck dried for 10 minute under nitrogen and dried for 12 h under vacuum at room temperature to afford white solid (0.9 g, 54%).

Workup

  1. temperatureto cool slowly to room temperature
  2. customThe slurry formed
  3. filtrationfiltered under nitrogen
  4. customdried for 10 minute under nitrogen
  5. customdried for 12 h under vacuum at room temperature

Sources & evidence

ORD record
ord-7e1afbc57b4e4260a552384077e2c544
Source dataset
uspto-grants-2015_06
Patent number
US09056816B2

Reaction notes

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