Dipropylamine → HCID 86753951, compound

HRID 1418926Notes

Reaction equation

HRID 1418926 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].IN1C(=O)CCC1=O.[CH2:31]([NH:34][CH2:35][CH2:36][CH3:37])[CH2:32][CH3:33]>C(O)(=O)C>[CH2:31]([N:34]([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)[CH2:35][CH2:36][CH3:37])[CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 120273N-IodosuccinimideHCID 86753949HCID 86753949, compound

Product 1

HCID 86753951HCID 86753951, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.60 g (0.00832 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 2.8 g (0.0125 mol) of N-iodosuccinimide while gassing with argon. After stirring at room temperature for 46 hrs. the dark suspension obtained was completely freed from the solvents and dried azeotropically several times with toluene. The dark solid residue was suspended in 100 ml of THF, treated with 11.4 ml (0.0832 mol) of dipropylamine and stirred at room temperature for 18 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, the orange-brownish product was chromatographed over basic Alox (grade III) with dichloromethane/ethyl acetate 4:1 as the eluent and recrystallized from hot isopropyl ether. There was obtained 1.0 g (25%) of (S)-1-(5-dipropylaminomethyl-oxazol-2-yl)-11,11a-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. 133°-135° and [α]D20 =-32.3° (CHCl3, c=1%).

Workup

  1. customthe dark suspension obtained
  2. dry with materialdried azeotropically several times with toluene
  3. stirringstirred at room temperature for 18 hrs
  4. customThe suspension obtained
  5. customthe residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid
  6. extractionextracted
  7. extractionextracted with ethyl acetate
  8. concentrationThe organic phase was concentrated
  9. customthe orange-brownish product was chromatographed over basic Alox (grade III) with dichloromethane/ethyl acetate 4:1 as the eluent
  10. customrecrystallized from hot isopropyl ether

Sources & evidence

ORD record
ord-09288f28abbf4f6ab4abdbc28a24fa35
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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