Hydrochloric Acid → HCID 56592010, compound

HRID 714472Notes

Reaction equation

HRID 714472 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][OH:36])=[CH:29][CH:28]=2)[C:22]([C:37]#[N:38])=[C:21](SC2C=CC=CC=2)[N:20]=1.Cl>COCCOC.O>[NH2:18][C:19]1[N:20]=[C:21]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)[C:22]([C:37]#[N:38])=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][OH:36])=[CH:31][CH:32]=2)[C:24]=1[C:25]#[N:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 185629Benzoic acid, 3-(hydroxymethyl)-HCID 23665647Potassium tert-butoxideHCID 66630499HCID 66630499, compound

Product 1

HCID 56592010HCID 56592010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

1.65 g (14.68 mmol) of potassium tert-butoxide were suspended in 15 ml of 1,2-dimethoxyethane. After addition of 0.97 g (5.87 mmol) of 3-(hydroxymethyl)benzenecarboxylic acid (Example 66A) and 1.14 g (2.94 mmol) of 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 35A), the mixture was stirred at 60° C. overnight. After cooling of the reaction mixture, 50 ml of water were added. With ice-cooling, the clear solution was acidified to pH 1 using conc. hydrochloric acid. The aqueous phase was decanted from the viscous precipitate formed. The residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid). The aqueous phase was evaporated and the residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. additionwere added
  2. temperatureWith ice-cooling
  3. customThe aqueous phase was decanted from the viscous precipitate
  4. customformed
  5. customThe residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)
  6. customThe aqueous phase was evaporated
  7. customthe residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7464d2b520af442fa5391e86479e772f
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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