2-Aminothiazole → HCID 64318486, compound

HRID 2243440Notes

Reaction equation

HRID 2243440 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:11].CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:43][C:44]1[S:45][CH:46]=[CH:47][N:48]=1>CN(C=O)C.ClCCCl.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:43][C:44]2[S:45][CH:46]=[CH:47][N:48]=2)=[O:8])=[CH:4][C:3]=1[Cl:11]

Participants

9

Reactant 5

HCID 21552-AminothiazoleHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 64318486HCID 64318486, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Amino-3-chloro-benzoic acid (19.8 mmol) was dissolved in DMF (10 mL) and 1,2-dichloroethane (80 mL). DIPEA (19.8 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (19.8 mmol), 1-hydroxybenzotriazole (19.8 mmol) and 2-aminothiazole (19.8 mmol) was added, and the reaction mixture was stirred at 60° C. over night. The volume was reduced in vacuo, and water (60 mL) was added. The mixture was extracted with ethyl acetate, the organic phase was washed with NH4Cl (aq., sat.), dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica using gradient elution (heptane/ethyl acetate).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with NH4Cl (aq., sat.)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica using gradient elution (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-105b4ce4a86f43c19c9f348276124c9f
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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