HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dihydro-1-benzofuran-7-carbaldehyde → (1H-Benzimidazol-2-ylmethyl)-(2,3-dihydro-benzofuran-7-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dihydro-1-benzofuran-7-carbaldehyde | HCID 2795018 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-[(5,6,7,8-Tetrahydroquinolin-8-ylamino)-methyl]-benzimidazole-1-carboxylic acid tert-butyl ester | HCID 21985081 | — |
| Product | (1H-Benzimidazol-2-ylmethyl)-(2,3-dihydro-benzofuran-7-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine | HCID 21984995 | — |
Reaction Steps
Following General Procedure B: To a solution of 2,3-dihydrobenzofuran-7-carboxaldehyde (53.6 mg, 0.362 mmol) and [1-(tert-butoxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (136 mg, 0.361 mmol) CH2Cl2 (5 mL) was added NaBH(OAc)3 (112 mg, 0.528 mmol) and the mixture stirred overnight. Purification of the crude product by radial chromatography on silica gel (1 mm TLC plate, 125:1:1 CH2Cl2:CH3OH:NH4OH) to gave the desired freebase (48 mg, 33%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807694B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-9897a58c87d24fc1b88bad3646cb5811 |
| Source note | uspto-grants-2010_10 |