Ammonium Acetate → HCID 178428414, compound

HRID 408547Notes

Reaction equation

HRID 408547 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.[CH3:18][C:19]1([CH3:27])[CH2:24][O:23][C:22](=[O:25])[CH2:21][C:20]1=O.C([O-])(=O)C.[NH4+:32]>>[CH3:16][C:15]1[NH:32][C:20]2[C:19]([CH3:27])([CH3:18])[CH2:24][O:23][C:22](=[O:25])[C:21]=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

4

Reactant 3

HCID 517165Ammonium AcetateHCID 585917345,5-dimethyldihydro-2H-pyran-2,4(3H)-dione2×HCID 178467936HCID 178467936, compound

Product 1

HCID 178428414HCID 178428414, compound

Procedure

The title compound was prepared from 200 mg (0.888 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)-methylidene]-3-oxobutanenitrile (Example 2A), 126 mg (0.888 mmol) 5,5-dimethyldihydro-2H-pyran-2,4(3H)-dione [preparation: US 2006/0014826-A1 (Intermediate 6)] and 102 mg (1.332 mmol) ammonium acetate in analogy to the procedure described in Example 1 yielding 51 mg (16% of th.) after purification by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) followed by flash chromatography (silica gel; ethyl acetate/cyclohexane gradient, final mixture 5:1 v/v).

Workup

  1. customafter purification by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-86d0fa5f7f884ac280df69d005047799
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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