Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Furfurylamine | HCID 3438 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Chlorosulfonyl isocyanate | HCID 70918 | — |
| Reactant | 3-(7-Amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)-1,8-naphthyridin-2(1H)-one | HCID 135430710 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 136347300 | HCID 136347300 | 15% |
Reaction Steps
A solution of chlorosulfonyl isocyanate (4.9 μL, 0.0562 mmol) in dichloromethane (2 mL) was treated dropwise with furfurylamine (5 μL, 0.0562 mmol) at 25° C., stirred at 25° C. for 30 min, treated with a solution of product of Example 205 (20 mg, 0.0468 mmol) and triethylamine (26 μL, 0.187 mmol) in dichloromethane (2 mL) and stirred for 24 hours at 25° C. The reaction mixture was partitioned between dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL). The resulting organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the title compound (15%). MS m/z 630 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07902203B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-20689dc2cbce4b728e236f4d70fe2b51 |
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| Source note | uspto-grants-2011_03 |
|---|
