Acetamide → 9-(2-Methyloxazol-4-yl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532943Notes

Reaction equation

HRID 532943 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9]1[C:19](=[O:20])[CH2:18][NH:17][C:16](=[O:21])[CH:15]=[C:10]12)=O.[C:22]([NH2:25])(=[O:24])[CH3:23]>>[CH3:23][C:22]1[O:24][CH:2]=[C:3]([C:5]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:6]=2[CH2:7][CH2:8][N:9]2[C:19](=[O:20])[CH2:18][NH:17][C:16](=[O:21])[CH:15]=[C:10]23)[N:25]=1

Participants

3

Reactant 2

HCID 178AcetamideHCID 867113869-(2-Bromoacetyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

Product 1

HCID 867113879-(2-Methyloxazol-4-yl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneYield 53.9%

Conditions

Temperature
130 °C

Procedure

111-3. A flask was charged with 9-(2-bromoacetyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (230 mg, 0.66 mmol) and acetamide (233 mg, 3.95 mmol) and the solid mixture was heated to 130° C. for 15 min. The resulting brown liquid mass was partitioned in AcOEt and H2O. The org. phase was separated, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/MeOH (100:0 to 90:10) gave the title compound (110 mg) as a beige powder. UPLC-MS: MS 310.2 (M+H+); UPLC rt 0.67 min.

Workup

  1. customThe resulting brown liquid mass was partitioned in AcOEt
  2. customphase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2, AcOEt/MeOH (100:0 to 90:10)

Sources & evidence

ORD record
ord-06cdd00835854b359766fd54fbf55c45
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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