Formamidine acetate → HCID 20605616, compound

HRID 481082Notes

Reaction equation

HRID 481082 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=O)[CH:21]([C:24](=O)[CH3:25])[CH2:20][CH2:19][CH2:18][C:8]=2[N:9](C(OC(C)(C)C)=O)[CH:10]=1)=[O:5])[CH3:2].C(O)(=O)C.[CH:31]([NH2:33])=[NH:32]>CCO>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22]3[N:32]=[CH:31][N:33]=[C:24]([CH3:25])[C:21]=3[CH2:20][CH2:19][CH2:18][C:8]=2[NH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 206056545-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 20605616HCID 20605616, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube are 5-acetyl-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.1 mmol) and formamidine acetate (5.5 mmol) and 10 mL EtOH. The mixture is heated at 120° C. for 48 hours. The solvent is evaporated in vacuo and the residue is taken up in CH2Cl2 and washed two times with NaHCO3 (aq). The organic layer is dried over Na2SO4 and evaporated in vacuo and the residue chromatographed using 10% MeOH in CH2Cl2 as mobile phase to yield 7-Methyl-3,4,5,6-tetrahydro-3,8,10-triaza-benzo[e]azulene-1-carboxylic acid ethyl ester (36%). LRMS 271.1 found (M+1) 272

Workup

  1. customIn a sealed tube are
  2. customThe solvent is evaporated in vacuo
  3. washwashed two times with NaHCO3 (aq)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. customevaporated in vacuo
  6. customthe residue chromatographed

Sources & evidence

ORD record
ord-965bf5762c554a3d8257cb9b0f375ded
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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