Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 78077574 | HCID 78077574 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86725362 | HCID 86725362 | 84.2% |
Reaction Steps
To a solution of 3-[(4-oxo-5-(3-(carboxymethyloxy)benzylidene)-2-thioxothiazolidin-3-yl)amino]-1,2-benzothiazole 1,1-dioxide (34 mg) obtained in Example 174 and benzylamine (8 mg) in N,N-dimethylformamide (1 ml) were added 1-hydroxybenzotriazole (10 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (14 mg) with stirring under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water (20 ml), and the mixture was extracted with ethyl acetate (30 ml). The extract was washed successively with 0.5M aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 3-[(4-oxo-5-(3-(benzyl aminocarbonylmethyloxy)benzylidene)-2-thioxothiazolidin-3-yl)amino]-1,2-benzothiazole 1,1-dioxide (34 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09056862B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-a5dcbb1550e14da3b6d44f5b71b5b739 |
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| Source note | uspto-grants-2015_06 |
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