Triethylamine → HCID 178447372, compound

HRID 1591506Notes

Reaction equation

HRID 1591506 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:4]1=[O:32].C(N(CC)CC)C.[CH3:40][C:41]([CH3:46])=[CH:42][C:43](Cl)=[O:44]>C(Cl)Cl>[CH3:40][C:41]([CH3:46])=[CH:42][C:43]([NH:2][C@@H:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:4]1=[O:32])=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 178479246HCID 178479246, compound

Product 1

HCID 178447372HCID 178447372, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-96e763c152ef491699916c1e62f6aaf2
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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