Hydrochloric Acid → HCID 178461991, compound

HRID 46151Notes

Reaction equation

HRID 46151 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([NH:10][C:11]1[S:12][C:13]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)([CH3:17])[C:14](=[O:16])[N:15]=1)[CH3:9].[OH-:26].[K+].Cl>CC(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([NH:10][C:11]1[S:12][C:13]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([NH2:23])=[O:26])=[CH:24][CH:25]=2)([CH3:17])[C:14](=[O:16])[N:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178461988HCID 178461988, compound

Product 1

HCID 178461991HCID 178461991, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

The mixture of 4-(2-((S)-1-(2-fluorophenyl)ethylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)benzonitrile (0.080 g, 0.23 mmol) and potassium hydroxide (VWR, 0.17 g, 2.9 mmol) and t-BuOH (2 mL) was gradually heated to 85° C. The solid gradually dissolved and the mixture became a solution. After 1 h, the reaction was added to 2N HCl until the pH was ca. 7-8. The mixture was extracted three times with CH2Cl2, and the combined organic layers was dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by silica gel chromatography. MS: 372 (M+1), 370 (M−1).

Workup

  1. dissolutionThe solid gradually dissolved
  2. extractionThe mixture was extracted three times with CH2Cl2
  3. dry with materialthe combined organic layers was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-69478610cbf7466ea75e81d02a2d4c05
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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