2-Aminothiazole → HCID 64318487, compound

HRID 2243442Notes

Reaction equation

HRID 2243442 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Br: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[Br:11]

Participants

9

Reactant 5

HCID 21552-AminothiazoleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2389354-Amino-3-bromobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 64318487HCID 64318487, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Amino-3-bromo-benzoic acid (18.5 mmol) was dissolved in DMF (10 mL) and 1,2-dichloroethane (80 mL). DIPEA (18.5 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (18.5 mmol), 1-hydroxybenzotriazole (18.5 mmol) and 2-aminothiazole (18.5 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-1c9af93e9e4640d5b0bdc0dd9107bcb8
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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