Hydrochloric Acid → HCID 56592009, compound

HRID 714471Notes

Reaction equation

HRID 714471 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][C@H:9]([C:11]2[CH:12]=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:21]#[N:22])=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][OH:32])=[CH:25][CH:24]=2)[C:3]=1[C:33]#[N:34].[OH-].[Li+].Cl>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([S:8][C@H:9]([C:11]2[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:21]#[N:22])=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][OH:32])=[CH:25][CH:24]=2)[C:3]=1[C:33]#[N:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89736147HCID 89736147, compound

Product 1

HCID 56592009HCID 56592009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

85 mg (0.179 mmol) of rac-methyl 3-[(1S)-1-({6-amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]pyridin-2-yl}sulfanyl)ethyl]benzenecarboxylate (Example 62A) were dissolved in 4 ml of tetrahydrofuran. 8.58 mg (0.358 mmol) of lithium hydroxide were added, and the mixture was then stirred at RT overnight. The reaction solution was adjusted to pH 4 using 1N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and evaporated.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3e4dd883ad1c454cbface4e2ad86a998
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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