Triethylamine → HCID 69959150, compound

HRID 893863Notes

Reaction equation

HRID 893863 reaction equation
[S:1]1[C:5]23[CH:13]=[CH:12][CH:11]=[CH:10][C:6]2=[N:7][CH:8]=[CH:9][C:4]3=[C:3]([C:14]([OH:16])=O)[CH2:2]1.[ClH:17].C(OC([NH:28][CH2:29][CH2:30][NH2:31])=O)C1C=CC=CC=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[ClH:17].[NH2:28][CH2:29][CH2:30][NH:31][C:14]([C:3]1[CH2:2][S:1][C:5]23[CH:13]=[CH:12][CH:11]=[CH:10][C:6]2=[N:7][CH:8]=[CH:9][C:4]=13)=[O:16]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochlorideHCID 19891249HCID 19891249, compound

Product 1

HCID 69959150HCID 69959150, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 10 ml of dimethylformamide (DMF) were suspended 487 mg of benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid synthesized in Example 17 and 508 mg of benzyloxycarbonylethylenediamine hydrochloride ##STR58## and after adding thereto 307 μl of triethylamine, the mixture was cooled to 0° C. Then, 660 mg of diphenylphosphorylazide (DPPA) and 336 μl of triethylamine were added thereto and the mixture was stirred for one hour under ice-cooling and stirred overnight at room temperature. The reaction mixture was diluted with 200 ml of ethyl acetate, washed with an aqueous 5% citric acid solution, an aqueous 5% sodium hydrogencarbonate solution, and then a saturated aqueous sodium chloride solution, and then dried by sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure, the residue was dissolved in 10 ml of acetic acid and after adding thereto 5 ml of an acetic acid solution of 25% hydrogen bromide, the mixture was stirred for 2 hours at 50° C. The reaction mixture was diluted with 200 ml of water and washed twice with ether. After adjusting the pH thereof to 11 with sodium hydroxide, the reaction mixture was extracted thrice with chloroform and the extract was dried by sodium sulfate. Chloroform was distilled off under reduced pressure and the residue was diluted with 100 ml of ethyl acetate. Then, 2 ml of a mixture of 1N hydrochloric acid in ethyl acetate was added dropwise to the residue and crystals thus deposited were collected by filtration to provide 230 mg (yield of 37%) of N-(2-aminoethyl)-benzo[b]thieno[2,3-c]pyridine-3-carboamide.hydrochloride.

Workup

  1. additionafter adding
  2. temperaturecooling
  3. stirringstirred overnight at room temperature
  4. washwashed with an aqueous 5% citric acid solution
  5. dry with materialan aqueous 5% sodium hydrogencarbonate solution, and then a saturated aqueous sodium chloride solution, and then dried by sodium sulfate
  6. distillationThen, ethyl acetate was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in 10 ml of acetic acid
  8. additionafter adding
  9. stirring5 ml of an acetic acid solution of 25% hydrogen bromide, the mixture was stirred for 2 hours at 50° C
  10. additionThe reaction mixture was diluted with 200 ml of water
  11. washwashed twice with ether
  12. extractionto 11 with sodium hydroxide, the reaction mixture was extracted thrice with chloroform
  13. dry with materialthe extract was dried by sodium sulfate
  14. distillationChloroform was distilled off under reduced pressure
  15. additionthe residue was diluted with 100 ml of ethyl acetate
  16. additionThen, 2 ml of a mixture of 1N hydrochloric acid in ethyl acetate was added dropwise to the residue and crystals
  17. filtrationthus deposited were collected by filtration

Sources & evidence

ORD record
ord-bbe622002713481c9b9347b7feeb4e93
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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