Ammonium Acetate → HCID 178428411, compound

HRID 408548Notes

Reaction equation

HRID 408548 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[C:12](/[C:15](=O)[CH3:16])\[C:13]#[N:14])[CH:9]=2)[NH:4][N:3]=1.O[C:19]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C:21](=[O:31])[CH:20]=1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[CH3:16][C:15]1[NH:36][C:19]2[CH2:23][NH:22][C:21](=[O:31])[C:20]=2[CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 54682595tert-Butyl 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylateHCID 178467936HCID 178467936, compound

Product 1

HCID 178428411HCID 178428411, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 200 mg (0.888 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A), 353 mg (0.888 mmol, approx. 50% purity) tert-butyl 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate [W.-R. Li et al., J. Org. Chem. 2002, 67, 4702-4706] and 102 mg (1.332 mmol) ammonium acetate in acetic acid (4 ml) was stirred at 100° C. for 45 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified first by flash chromatography (silica gel; dichloromethane/methanol gradient, final mixture 10:1 v/v) and then by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to give 31 mg (11% of th.) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified first by flash chromatography (silica gel; dichloromethane/methanol gradient, final mixture 10:1 v/v)

Sources & evidence

ORD record
ord-4c3cf194651e4d07abb751d9c65cda77
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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