2-Aminothiazole → HCID 57535437, compound

HRID 1455658Notes

Reaction equation

HRID 1455658 reaction equation
Br[CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[C:23]([C:31]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32])[CH:24]=[C:25]3[C:30]=2[N:29]=[CH:28][CH:27]=[CH:26]3)[CH:16]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>CN(C=O)C.O.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH3:37][C:31]([C:23]1[CH:24]=[C:25]2[C:30](=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:2]4[N:43]5[C:39]([S:40][CH:41]=[CH:42]5)=[N:38][C:3]=4[C:5]4[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][CH:6]=4)[CH:16]=3)[CH:22]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)([S:33]([CH3:36])(=[O:35])=[O:34])[CH3:32]

Participants

7

Reactant 2

HCID 21552-AminothiazoleHCID 86608354HCID 86608354, compound

Product 1

HCID 57535437HCID 57535437, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the alphabromoketone from EXAMPLE 1, step 4 (1.0 eq) in DMF (0.1M) was added 2-aminothiazole (1.6 eq). The mixture was heated at 120° C. for 1 h, cooled, diluted with water, saturated NaHCO3 solution and EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Toluene:EtOAc, 1:3) to afforded the title compound.

Workup

  1. temperaturecooled
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Toluene:EtOAc, 1:3)

Sources & evidence

ORD record
ord-fcfcb9071a534edf8f7b7ff55dc83d26
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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