Cyclopropanecarboxylic acid → HCID 86612146, compound

HRID 1867957Notes

Reaction equation

HRID 1867957 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:12]1([C:15]([OH:17])=O)[CH2:14][CH2:13]1.C(N(CC)[CH:22]([CH3:24])[CH3:23])(C)C.CN([C:30]([O:34]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[CH:12]1([C:15]([NH:1][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][C:30]([CH:22]4[CH2:24][CH2:23]4)=[O:34])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:17])[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 334622-Amino-6-benzothiazolol2×HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86612146HCID 86612146, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-aminobenzothiazol-6-ol (intermediate 1) (850 mg, 4.6 mmol), cyclopropanecarboxylic acid (1.564 g, 18.1 mmol), N,N-diisopropylethylamine (3.6 ml, 24.4 mmol) and HBTU (4.1 g, 5.53 mmol) in 40 ml of dimethyl-formamide, in a 100 ml round-bottomed flask equipped with a magnetic bar, is stirred at room temperature for 16 hours. 150 ml of water are added to the reaction medium, the mixture is extracted with ethyl acetate and the extracts are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated to dryness. The residue obtained is washed with ethyl acetate to give 893 mg of cyclopropanecarboxylic acid 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester. LC/MS: [M+H]+=303.18, retention time=3.53 min. A solution of lithium hydroxide monohydrate (200 mg, 4.768 mmol) in 50 ml of methanol and 5 ml of water is added to this product. The reaction medium is refluxed with stirring for 1 hour. The reaction medium is concentrated, acidified to pH 1 with 2N hydrochloric acid solution, diluted with 100 ml of water and extracted with ethyl acetate. The organic phase is washed with water and then with saturated sodium chloride solution and evaporated to dryness to give 500 mg of cyclopropanecarboxylic acid (6-hydroxybenzothiazol-2-yl)amide in a yield of 72% (beige-colored powder).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. washis washed with ethyl acetate

Sources & evidence

ORD record
ord-cc30650b93924540ad99f77633ac2019
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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