Triethylamine → HCID 178447372, compound

To a suspension of 1.18 g (2.64 mmol) of 3(R)-amino-1,3,4,5-tetrahydro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2H-1-benzazepin-2-one, hydrochloride (Example 4, Step C) in 30 mL of methylene chloride under nitrogen at -15° C. was added 0.923 mL (2.64 mmol) of triethylamine followed by 0.294 mL (2.64 mmol) of 3,3-dimethylacryloyl chloride. The reaction mixture was stirred at -15° C. for 2 hours then quenched by the addition of 1N hydrochloric acid. The mixture was diluted with 50 mL of methylene chloride and washed with 50 mL of 1N hydrochloric acid and brine. The organic layer was removed and concentrated to dryness under vacuum. The residue was redissolved in 30 mL of methanol and treated with 1.5 mL of 9N hydrochloric acid. After stirring for 30 minutes, the mixture was concentrated to dryness under vacuum to give 1.3 g (2.63 mmol, 99%) of the product as a white solid.

1. customthen quenched by the addition of 1N hydrochloric acid
2. additionThe mixture was diluted with 50 mL of methylene chloride
3. washwashed with 50 mL of 1N hydrochloric acid and brine
4. customThe organic layer was removed
5. concentrationconcentrated to dryness under vacuum
6. dissolutionThe residue was redissolved in 30 mL of methanol
7. additiontreated with 1.5 mL of 9N hydrochloric acid
8. stirringAfter stirring for 30 minutes
9. concentrationthe mixture was concentrated to dryness under vacuum

ORD record

ord-96e763c152ef491699916c1e62f6aaf2

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05206235