Fumaric Acid → HCID 71534479, compound

HRID 1523731Notes

Reaction equation

HRID 1523731 reaction equation
[Cl:1][C:2]1[C:3]([NH2:26])=[C:4]2[C:9](=[C:10]([C:12]3[O:13][C:14]([CH:17]4[CH2:22][CH2:21][N:20]([CH:23]5[CH2:25][CH2:24]5)[CH2:19][CH2:18]4)=[N:15][N:16]=3)[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[C:3]([NH2:26])=[C:4]2[C:9](=[C:10]([C:12]3[O:13][C:14]([CH:17]4[CH2:18][CH2:19][N:20]([CH:23]5[CH2:25][CH2:24]5)[CH2:21][CH2:22]4)=[N:15][N:16]=3)[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.[Cl:1][C:2]1[C:3]([NH2:26])=[C:4]2[C:9](=[C:10]([C:12]3[O:13][C:14]([CH:17]4[CH2:18][CH2:19][N:20]([CH:23]5[CH2:25][CH2:24]5)[CH2:21][CH2:22]4)=[N:15][N:16]=3)[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 71534480HCID 71534480, compound

Product 1

HCID 71534479HCID 71534479, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-chloro-8-[5-(1-cyclopropyl piperidin-4-yl)-[1,3,4]oxadiazol-2-yl]chroman-5-yl amine (14 grams, 37.3 mmol, obtained in the above step) in ethanol (280 mL) was heated to reflux until clear solution obtained. The mixture was cooled to room temperature and fumaric acid (4.32 grams, 37.3 mmol) was added. The reaction mixture was heated to reflux for 1 hour. The volatiles were removed under reduced pressure and the furmarate salt, thus obtained, was recrystallized from isopropanol to obtain 6-Chloro-8-[5-(1-cyclopropyl piperidin-4-yl)-[1,3,4]oxadiazol-2-yl]chroman-5-yl amine hemi fumarate (14.0 grams).

Workup

  1. temperaturewas heated
  2. temperatureto reflux until clear solution
  3. customobtained
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux for 1 hour
  6. customThe volatiles were removed under reduced pressure
  7. customthe furmarate salt, thus obtained
  8. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-74967d977dd04ecbbcb6b112e3c54d68
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

Loading…