Dimethylformamide → HCID 53767971, compound

HRID 1378065Notes

Reaction equation

HRID 1378065 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N([CH:31]([CH3:33])[CH3:32])C(C)C)C.I[CH2:35][CH2:36][CH2:37][CH3:38].[CH3:39]N(C)C=O>>[CH2:35]([N:1]([CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][CH:13]4[C:12]=23)[O:5][N:4]=1)[CH2:39][CH2:33][CH2:31][CH3:32])[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 81531DiisopropylethylamineHCID 54124626HCID 54124626, compound

Product 1

HCID 53767971HCID 53767971, compound

Procedure

2 g (6.2 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 30 ml of N,N-dimethylformamide, 3.7 ml (21.7 mmol) of N-ethyldiisopropylamine and 1.6 ml (14.3 mmol) of 1-iodobutane were stirred at room temperature for 6 hours and at 80° for 1.5 hours. The reaction mixture was evaporated and the residue was chromatographed on 180 g of silica gel while eluting with methylene chloride/ethyl acetate 7/3. By concentrating the uniform fractions there were obtained 1.6 g (59%) of S)-1-(3-di-butylaminomethyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on 180 g of silica gel
  3. washwhile eluting with methylene chloride/ethyl acetate 7/3
  4. concentrationBy concentrating the uniform fractions

Sources & evidence

ORD record
ord-178c587298d14dd6993596bf14dc6083
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…