Gyki 52895 → Acetamide, N-acetyl-N-(4-(7-acetyl-8,9-dihydro-8-methyl-7H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)phenyl)-

HRID 1683702Notes

Reaction equation

HRID 1683702 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(O[C:27](=[O:29])[CH3:28])(=O)C>>[C:17]([N:1]([C:27](=[O:29])[CH3:28])[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[N:10]([C:16](=[O:21])[CH3:15])[N:9]=2)=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 3539Gyki 52895HCID 7918Acetic Anhydride

Product 1

HCID 3072682Acetamide, N-acetyl-N-(4-(7-acetyl-8,9-dihydro-8-methyl-7H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)phenyl)-

Procedure

2.0 g (6.7 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine were refluxed with 40 ml of acetic anhydride for 3 hours, then it was evaporated to dryness under reduced pressure. The crystalline residue was transferred with 25 ml of water to a filter and washed with 5×3 ml of water. After drying 2.79 g of the raw triacetyl derivative were obtained. After washing with 20 ml of isopropanol and drying at 100° C. 2.39 g (84.6 of the pure aimed product were obtained, m.p. 224°-227° C.

Workup

  1. customit was evaporated to dryness under reduced pressure
  2. filtrationa filter
  3. washwashed with 5×3 ml of water
  4. dry with materialAfter drying 2.79 g of the raw triacetyl derivative
  5. customwere obtained
  6. washAfter washing with 20 ml of isopropanol
  7. customdrying at 100° C

Sources & evidence

ORD record
ord-30143e85f85a47d7ae9d70b80e34e758
Source dataset
uspto-grants-1997_06
Patent number
US05639751

Reaction notes

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