1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[3-(4-Chloro-phenyl)-ureido]-benzothiazole-6-carboxylic acid (2-oxo-2,3-dihydro-benzooxazol-6-yl)-amide

HRID 2193480Notes

Reaction equation

HRID 2193480 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[NH:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]([OH:22])=O)[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:34]=[CH:33][C:28]2[NH:29][C:30](=[O:32])[O:31][C:27]=2[CH:26]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[O:32]=[C:30]1[NH:29][C:28]2[CH:33]=[CH:34][C:25]([NH:24][C:20]([C:18]3[CH:17]=[CH:16][C:14]4[N:15]=[C:11]([NH:10][C:9]([NH:8][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[O:23])[S:12][C:13]=4[CH:19]=3)=[O:22])=[CH:26][C:27]=2[O:31]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 866613812-[3-(4-Chloro-phenyl)-ureido]-benzothiazole-6-carboxylic acid

Product 1

HCID 469405502-[3-(4-Chloro-phenyl)-ureido]-benzothiazole-6-carboxylic acid (2-oxo-2,3-dihydro-benzooxazol-6-yl)-amideYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Starting material 35 (300 mg, 45% content, 0.4 mmol) and 6-Amino-3H-benzooxazol-2-one (30, 58 mg, 0.4 mmol) were dissolved in 2 ml of dry DMF. Then EDCI (96 mg, 0.5 mmol) and HOBt (76 mg, 0.5 mmol) were added. The reaction was stirred at ambient temperature over night. It was then purred into water and the resulting precipitate was filtered. The isolated precipitate was then stirred in 100 ml warm methanol and the non-soluble crystals filtered and washed with methanol. Thereby the desired product 36 (130 mg, 0.271 mmol, 70%) could be isolated.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. stirringThe isolated precipitate was then stirred in 100 ml
  3. temperaturewarm methanol
  4. filtrationthe non-soluble crystals filtered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-3a609a0ce8a14ee0bb3461342e56bce0
Source dataset
uspto-grants-2012_12
Patent number
US08329907B2

Reaction notes

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