Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 11524373 | HCID 11524373 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 11582260 | HCID 11582260 | — |
Reaction Steps
N-(4-carboxyphenyl)-4-(3-chloropyridin-2-yl)-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxamide (100 mg) obtained in Example 1-035 was dissolved in N,N-dimethylformamide (2 ml), ammonium chloride (65 mg), 1-hydroxybenzotriazole (56 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (70 mg) and triethylamine (0.20 ml) were added in this order, and the mixture was stirred at room temperature for 10 hours. After adding water and saturated sodium hydrogencarbonate solution to the reaction mixture, the mixture was partitioned by adding ethyl acetate. After ethyl acetate layer was washed with water, concentrated and dried, the concentrate was suspended in and washed with water, the white solid substance was collected by filtration and dried to obtain the title compound (80 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08008292B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-32995ab0defc468d87b696f0a6859310 |
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| Source note | uspto-grants-2011_08 |
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