Acetic Acid → HCID 178468663, compound

HRID 1796646Notes

Reaction equation

HRID 1796646 reaction equation
[Li]CCCC.[CH3:6][C:7]#[N:8].C(O[C:12]([C:14]1[N:15]([N:24]=[CH:25]N(C)C)[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:18]=1)=[O:13])C.CC(O)=O>C1COCC1>[CH2:22]([O:21][C:19]([C:16]1[N:15]2[N:24]=[CH:25][C:6]([C:7]#[N:8])=[C:12]([OH:13])[C:14]2=[CH:18][CH:17]=1)=[O:20])[CH3:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 693265321-(dimethylamino-methyleneamino)-1H-pyrrole-2,5-dicarboxylic acid diethyl esterHCID 178418339Butyllithium

Product 1

HCID 178468663HCID 178468663, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of n-BuLi (1.6 M in hexanes) (290 μl, 0.465 mmol) in THF (1 ml) was added a solution of CH3CN (19.1 mg, 0.465 mmol) in THF (2 ml) dropwise at 0° C. The mixture was stirred for 20 min, then a solution of 406D (62 mg, 0.221 mmol) in THF (5 ml) was added. After the mixture was stirred for 40 min, the reaction temperature was lowered to −78° C., AcOH (38 μl, 0.663 mmol) was added. The reaction mixture was then stirred at rt overnight. Solvent was removed, 406E (26 mg, 50%) was obtained as a yellowish solid after preparative HPLC purification. LCMS Found: (M+H)+=232.

Workup

  1. stirringAfter the mixture was stirred for 40 min
  2. customwas lowered to −78° C.
  3. stirringThe reaction mixture was then stirred at rt overnight
  4. customSolvent was removed

Sources & evidence

ORD record
ord-15e945e4c1074be3844fbc3385bfa948
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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