Acetic Anhydride → HCID 54459887, compound

HRID 442693Notes

Reaction equation

HRID 442693 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][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:23][C:24](OC(C)=O)=[O:25].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[C:24]([NH: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][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:25])[CH3:23]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 9839097HCID 9839097, compound

Product 1

HCID 54459887HCID 54459887, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4-(4H)-one (90 mg, 0.30 mmol) in CH2Cl2 (10 mL) was added Ac2O (0.30 mL, 3.2 mmol) and Et3N (0.60 mL, 4.3 mmol) at room temperature. The mixture was stirred at room temperature for 2 h, diluted with EtOAc (40 mL), washed with water, 2N NaOH water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography to afford the title compound as a white solid (70 mg, 0.21 mmol, 70%), mp: 177°-180° C. 1H NMR (CDCl3) 8.34 (s, 1H), 7.57 (s, 4H), 7.27 (s, 1H), 6.83 (s, 1H), 6.64 (s, 1H), 6.03 (s, 2H), 3.45 (s, 2H), 2.22 (s, 3H). Anal. calcd. for C18H15N3O4.(1/2)H2O: C, 62.42; H, 4.66; N, 12.13. Found: C, 62.60; H, 4.62; N, 11.57.

Workup

  1. washwashed with water, 2N NaOH water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d3169367cf404b329268994ed24ddc08
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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