Dimethylformamide → HCID 86751230, compound

HRID 1378038Notes

Reaction equation

HRID 1378038 reaction equation
NC[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]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[O:5][N:4]=1.[CH2:27](N(C(C)C)C(C)C)[CH3:28].[CH2:36](Br)C#C.C[N:41]([CH3:44])C=O>>[Cl:22][C:21]1[C:16]2[C:15](=[O:23])[N:14]3[CH2:24][CH2:25][CH2:26][C@H:13]3[C:12]3[N:11]([CH:10]=[N:9][C:8]=3[C:6]3[O:5][N:4]([CH3:36])[CH:3]([NH:41][CH2:44][C:27]#[CH:28])[N:7]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 81531DiisopropylethylamineHCID 22876576HCID 22876576, compound

Product 1

HCID 86751230HCID 86751230, compoundYield 29%

Procedure

3.7 g (10 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo-[2,1-c][1,4]benzodiazepin-9-one, 30 ml of N,N-dimethylformamide, 4.27 ml (25 mmol) of N-ethyldiisopropylamine and 2.38 g (20 mmol) of propargyl bromide were stirred at room temperature for 1 hour. After evaporating the reaction solution the residue was chromatographed on 430 g of silica gel while eluting with ethyl acetate/methanol 9/1. The uniform fractions having the lower Rf were evaporated. There were obtained 1.19 g (29%) of (S)-8-chloro-11,12,13,13a-tetrahydro-1-(3-propargylamino-methyl-1,2,4-oxadiazol-5-yl)-9H-imidazo[1,5-a]pyrrolo-[2,1-c][1,4]benzodiazepin-9-one of m.p. 144°-145°, which was converted into the hydrochloride of m.p. 189°-192°.

Workup

  1. customAfter evaporating the reaction solution the residue
  2. customwas chromatographed on 430 g of silica gel
  3. washwhile eluting with ethyl acetate/methanol 9/1
  4. customwere evaporated

Sources & evidence

ORD record
ord-851ad1f75c494eb3a78a5936246db13d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…