Hydrochloric Acid → HCID 56592010, compound

HRID 714474Notes

Reaction equation

HRID 714474 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][CH:30]=[CH:29][CH:28]=2)[C:22]([C:33]#[N:34])=[C:21](SC2C=CC=CC=2)[N:20]=1.Cl.C[O:44][CH2:45][CH2:46][O:47]C>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:33]#[N:34])=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:44][CH2:45][CH2:46][OH:47])=[CH:31][CH:32]=2)[C:24]=1[C:25]#[N:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 185629Benzoic acid, 3-(hydroxymethyl)-HCID 41651072-Amino-4-phenyl-6-phenylsulfanylpyridine-3,5-dicarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 56592010HCID 56592010, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4.72 g (42.06 mmol) of potassium tert-butoxide were suspended in 25 ml of 1,2-dimethoxyethane. After addition of 1.73 g (10.51 mmol) of 3-(hydroxymethyl)benzenecarboxylic acid (Example 66A) and 1.72 g (5.26 mmol) of 2-amino-4-phenyl-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 36A), 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 6-7 using conc. hydrochloric acid. The solution was evaporated. Purification was by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 1/1, finally acetonitrile/water 10/1).

Workup

  1. additionwere added
  2. temperatureWith ice-cooling
  3. customThe solution was evaporated
  4. customPurification

Sources & evidence

ORD record
ord-46a0d27483334464b0612eabc200768e
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

Loading…