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

HRID 926316Notes

Reaction equation

HRID 926316 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-14ed4f6123db49a19ee9d8b85315f0e4
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

Loading…