Propylamine → HCID 86753948, compound

HRID 1418924Notes

Reaction equation

HRID 1418924 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[N:8]=[CH:9][N:10]2[C:16]3[CH:17]=[CH:18][S:19][C:15]=3[C:14](=[O:20])[N:13]3[CH2:21][CH2:22][C@H:12]3[C:11]=12)=[O:6])[C:2]#[CH:3].I[N:24]1C(=O)[CH2:27][CH2:26][C:25]1=O.C(N)CC>C(O)(=O)C>[CH2:25]([NH:24][CH2:3][C:2]1[O:6][C:5]([C:7]2[N:8]=[CH:9][N:10]3[C:16]4[CH:17]=[CH:18][S:19][C:15]=4[C:14](=[O:20])[N:13]4[CH2:21][CH2:22][C@H:12]4[C:11]=23)=[N:4][CH:1]=1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 120273N-IodosuccinimideHCID 86753949HCID 86753949, compound

Product 1

HCID 86753948HCID 86753948, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.10 g (0.00992 mol) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]-diazepine-1-carboxylic acid prop-2-ynylamide in 60 ml of acetic acid was treated with 3.35 g (0.0149 mol) of N-iodosuccinimide while gassing with argon. After stirring at room temperature for 24 hrs. the dark suspension obtained was completely freed from the solvents and dried azeotropically several times with toluene. The dark residue was dissolved in 60 ml of THF, treated with 7.1 ml (0.0863 mol) of propylamine and stirred at room temperature for 6 hrs. The suspension obtained was completely freed from the solvents, the residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid and extracted. The aqueous-acidic phase was made basic and extracted with ethyl acetate. The organic phase was concentrated and the dark product was chromatographed over silica gel which dichloromethane/methanol 49:1 as the eluent. There was obtained 0.29 g (8%) of (S)-1-(5-propylaminomethyl-oxazol-2-yl)-11,11 a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as yellowish crystals; m.p. 145°-147°.

Workup

  1. customthe dark suspension obtained
  2. dry with materialdried azeotropically several times with toluene
  3. dissolutionThe dark residue was dissolved in 60 ml of THF
  4. stirringstirred at room temperature for 6 hrs
  5. customThe suspension obtained
  6. customthe residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid
  7. extractionextracted
  8. extractionextracted with ethyl acetate
  9. concentrationThe organic phase was concentrated
  10. customthe dark product was chromatographed over silica gel which dichloromethane/methanol 49:1 as the eluent

Sources & evidence

ORD record
ord-a5b9de3dee434a6eab2250034a2df773
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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