HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 2-Amino-6-(3-phenyl-2-propyn-1-yl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 2-Amino-4,5,6,7,8-pentahydrothiazolo[5,4-d]azepine | HCID 19985785 | — |
| Reactant | 3-(4-Isoquinolinyl)acrolein | HCID 54536698 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 2-Amino-6-(3-phenyl-2-propyn-1-yl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine | HCID 19985965 | — |
Reaction Steps
Prepared from 3-(4-isoquinolinyl)acrolein and 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine by reductive amination with sodium cyanoborohydride (in methanol in the presence of I equivalent of glacial acetic acid). The crude product is purified by column chromatography on silica gel (acetone/methanol/conc. ammonia =50:12:0.5). At first the title compound (A) is eluted. Yield: 4% of theory, Melting point: 205°-208° C. (ether).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05068325 |
| Source dataset | uspto-grants-1991_11 |
| ORD ID | ord-4caae74952694150aff7b8f7f4f97fa9 |
| Source note | uspto-grants-1991_11 |