Hydrochloric Acid → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(2R)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

HRID 403016Notes

Reaction equation

HRID 403016 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@H:18]3[CH2:22][O:21]C(C)(C)[O:19]3)=[CH:12][CH:11]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:28][C:29]2[N:30]=[C:31]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[O:32][CH:33]=2)[N:3]=1.Cl>C(O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][C@H:18]([OH:19])[CH2:22][OH:21])=[CH:14][CH:15]=2)[C:5]([C:25]#[N:26])=[C:4]([S:27][CH2:28][C:29]2[N:30]=[C:31]([C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)[O:32][CH:33]=2)[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67216338HCID 67216338, compound

Product 1

HCID 666718022-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(2R)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 127.1 g (221.4 mmol) of the compound from example 6A were suspended in 800 ml of ethanol and admixed with 800 ml of 37% strength hydrochloric acid. The mixture was stirred under reflux overnight. After cooling to room temperature, the precipitate formed was isolated by suction filtration, washed with ethanol and dried under reduced pressure at 50° C. overnight. This gave 108.3 g (92% of theory) of the target compound.

Workup

  1. temperatureunder reflux overnight
  2. customthe precipitate formed
  3. customwas isolated by suction filtration
  4. washwashed with ethanol
  5. customdried under reduced pressure at 50° C. overnight

Sources & evidence

ORD record
ord-b71d64f26808430189c880e52b86a9f5
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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