1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19101692, compound

HRID 1974633Notes

Reaction equation

HRID 1974633 reaction equation
Cl[C:2]1[C:3]([F:15])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[NH:7][CH:8]1[CH2:10][CH2:9]1.[C:16]([O:20][C:21](=[O:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1)([CH3:19])([CH3:18])[CH3:17].N12CCCN=C1CCCCC2>O.C(OCC)(=O)C>[CH:8]1([NH:7][C:6]2[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([F:15])=[C:2]([N:23]3[CH:24]=[CH:25][CH:26]=[C:22]3[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:27])[CH:11]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 15751484HCID 15751484, compound

Product 1

HCID 19101692HCID 19101692, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

5-Chloro-N-cyclopropyl-4-fluoro-2-nitroaniline (460 mg, 2 mmol) is heated to 80° for 40 hours with L-proline tert-butyl ester (342 mg, 2 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (304 mg, 2 mmol). The reaction mixture is then dissolved in a water/ethyl acetate mixture (1:1, 100 ml). The ethyl acetate phase is washed with 10 percent sodium chloride solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel (eluent: hexane/ethyl acetate 8:2). The product is crystallized from ether/n-hexane. There are obtained 94 mg (13%) of tert-butyl rac-1-[5-(cyclopropylamino)-2-fluoro-4-nitro-phenyl]pyrrole-2-carboxylate with a m.p. of 142°-143°.

Workup

  1. washThe ethyl acetate phase is washed with 10 percent sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel (eluent: hexane/ethyl acetate 8:2)
  5. customThe product is crystallized from ether/n-hexane

Sources & evidence

ORD record
ord-da18bcc6da9c4eb18aadaece50160a5d
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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