Azane;hydrate → HCID 57949214, compound

HRID 555249Notes

Reaction equation

HRID 555249 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:9])=[CH:6][C:5]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[CH:4][N:3]=1.O.[NH3:28]>C(O)(C)C>[NH2:28][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:9])=[CH:6][C:5]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 86635659HCID 86635659, compound

Product 1

HCID 57949214HCID 57949214, compoundYield 38.84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Chloro-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone (65 mg, 0.16 mmol) as a starting material was dissolved in isopropyl alcohol (3 ml), and ammonia water (10 ml) was added thereto. The mixture was heated for 3 hours in a Steel Bomb. After completion of the reaction, the reaction mixture was vacuum concentrated, and extracted with dichloromethane (30 ml) and water (10 ml). The organic layer was washed with brine, and dried over anhydrous MgSO4. The solid substance filtered off, and the filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=1/1) to obtain a desired yellow solid compound (24.0 mg, 38.84%).

Workup

  1. customAfter completion of the reaction
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane (30 ml) and water (10 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationThe solid substance filtered off
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (SiO2, n-Hex/EA=1/1)

Sources & evidence

ORD record
ord-0d13b3d843904cdeacf5181516094804
Source dataset
uspto-grants-2011_11
Patent number
US08053439B2

Reaction notes

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