Trifluoroacetic anhydride → HCID 67264401, compound

HRID 1687036Notes

Reaction equation

HRID 1687036 reaction equation
[CH3:1][CH:2]1[CH2:8][NH:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:5]=2[C:4](=[O:16])[NH:3]1.CC1NC2C=CC=C([N+]([O-])=O)[C:22]=2[C:21](=[O:32])NC1.C(N(C(C)C)CC)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH4+].[Cl-]>ClCCl>[C:21]([N:7]1[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:5]=2[C:4](=[O:16])[NH:3][CH:2]([CH3:1])[CH2:8]1)(=[O:32])[CH3:22]

Participants

7

Reactant 5

HCID 9845Trifluoroacetic anhydrideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 67263539HCID 67263539, compoundHCID 67263825HCID 67263825, compound

Product 1

HCID 67264401HCID 67264401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-Methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one and 2-Methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (350 mg, 1.58 mmol) was dissolved in dichloromethane (5 mL) and the solution was treated with diisopropylethylamine (0.330 mL, 1.89 mmol) and trifluoroacetic anhydride (332 mg, 1.58 mmol). The reactions were allowed to stir overnight at room temperature for approximately 3 hours. The mixture was then poured over saturated NH4Cl (30 mL) and extracted with dichloromethane (3×15 mL). Combined organic extracts were dried over Na2SO4, filtered and reduced. The crude product was then isolated and purified by flash column chromatography (0% ethyl acetate/hexanes-75% ethyl acetate hexanes) to afford 370 mg of 1-Acetyl-3-methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one and 1-Acetyl-2-methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a yellow oil.

Workup

  1. extractionextracted with dichloromethane (3×15 mL)
  2. dry with materialCombined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customThe crude product was then isolated
  5. custompurified by flash column chromatography (0% ethyl acetate/hexanes-75% ethyl acetate hexanes)

Sources & evidence

ORD record
ord-5fcbb445ea264d59bea2ff31df3f7e98
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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