1-Hydroxybenzotriazole → 2-[2-(4-Chloro-2-fluoro-phenyl)-acetylamino]-benzothiazole-6-carboxylic acid (2-oxo-2,3-dihydro-benzooxazol-6-yl)-amide

HRID 455013Notes

Reaction equation

HRID 455013 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[O:10])=[C:4]([F:24])[CH:3]=1.[NH2:25][C:26]1[CH:35]=[CH:34][C:29]2[NH:30][C:31](=[O:33])[O:32][C:28]=2[CH:27]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[O:33]=[C:31]1[NH:30][C:29]2[CH:34]=[CH:35][C:26]([NH:25][C:21]([C:19]3[CH:18]=[CH:17][C:15]4[N:16]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=5[F:24])[S:13][C:14]=4[CH:20]=3)=[O:22])=[CH:27][C:28]=2[O:32]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866613822-[2-(4-Chloro-2-fluoro-phenyl)-acetylamino]-benzothiazole-6-carboxylic acid

Product 1

HCID 469405482-[2-(4-Chloro-2-fluoro-phenyl)-acetylamino]-benzothiazole-6-carboxylic acid (2-oxo-2,3-dihydro-benzooxazol-6-yl)-amideYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Starting material 37 (60 mg, 0.2 mmol, 70% content) and 6-Amino-3H-benzooxazol-2-one (30, 25 mg, 0.2 mmol) were dissolved in 2 ml DMF. Then EDCl (38 mg, 0.2 mmol) and HOBt (31 mg, 0.2 mmol) were added. The reaction was stirred over night at ambient temperature, concentrated in vacuo and purified by prep HPLC (Method 1). By concentration of the pure fractions the desired product 38 (23 mg, 0.04 mmol, 24%) could be isolated.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by prep HPLC (Method 1)

Sources & evidence

ORD record
ord-8d817f441e4c481f9302ba7614b06267
Source dataset
uspto-grants-2013_07
Patent number
US08497283B2

Reaction notes

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