Dimethylformamide → HCID 54416509, compound

HRID 1378083Notes

Reaction equation

HRID 1378083 reaction equation
C(N([CH:7]([CH3:9])[CH3:8])C(C)C)C.[CH2:10](Br)[CH2:11][CH2:12][CH3:13].[NH2:15][CH2:16][C:17]1[O:21][C:20]([C:22]2[N:23]=[CH:24][N:25]3[C:31]4[CH:32]=[CH:33][S:34][C:30]=4[C:29](=[O:35])[N:28]4[CH2:36][CH2:37][C@H:27]4[C:26]=23)=[N:19][N:18]=1.[CH3:38]N(C)C=O>>[CH2:10]([N:15]([CH2:16][C:17]1[O:21][C:20]([C:22]2[N:23]=[CH:24][N:25]3[C:31]4[CH:32]=[CH:33][S:34][C:30]=4[C:29](=[O:35])[N:28]4[CH2:36][CH2:37][C@H:27]4[C:26]=23)=[N:19][N:18]=1)[CH2:38][CH2:9][CH2:7][CH3:8])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 81531DiisopropylethylamineHCID 22876586HCID 22876586, compound

Product 1

HCID 54416509HCID 54416509, compoundYield 39%

Procedure

17.4 ml (1 00 mmol) of N-ethyldiisopropylamine and 7.87 ml (73 mmol) of butyl bromide were added to a solution of 4 g (12.18 mmol) of (S)-1-(5-aminomethyl-1,3,4-oxadiazol-2-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 100 ml of dimethylformamide whereupon the mixture was stirred at 70° for 12 hours. The dimethylformamide was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed twice with methylene chloride and the organic phases were dried with sodium sulfate, filtered and evaporated. Chromatography (silica gel, ethyl acetate/methanol 10:1) yielded 2.1 g (39%) of (S)-1-(5-dibutylaminomethyl-1,3,4-oxadiazol-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 a colourless foam, Rf=0.4 (silica gel, ethyl acetate/methanol 10:1).

Workup

  1. customThe dimethylformamide was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed twice with methylene chloride
  4. dry with materialthe organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1c0af1fd5523461a841e59f764af9a20
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…