Diethyl (ethoxymethylene)malonate → HCID 178469508, compound

HRID 445787Notes

Reaction equation

HRID 445787 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>CC1C=CC=CC=1C>[CH2:26]([O:25][C:23]([C:22]1[CH:28]=[N:17][C:14]2[C:15]([C:21]=1[OH:20])=[N:16][C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:12][CH:13]=2)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 596196446-(3,4-Dimethoxy-phenyl)-pyridin-3-ylamine

Product 1

HCID 178469508HCID 178469508, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 6-(3,4-dimethoxy-phenyl)-pyridin-3-ylamine (Stage 249.1.4, 2.0 g, 8.69 mmol) and diethyl ethoxymethylenemalonate (Aldrich, Buchs, Switzerland, 2.087 ml, 10.42 mmol) in o-xylene (22 ml) was heated by microwaves at 150° C. for 45 min and at 250° C. for 9 h. The RM was cooled to rt and crystallized with diethylether. The suspension was filtered and the cake was triturated again in hot EtOAc and cooled after in the freezer. The suspension was filtered again. The cake was washed with EtOAc and dried in the vacuum oven to give the title compound as a brown solid. Used for next step without further purification. (HPLC: tR 2.58 min (Method A); M+H=355 MS-ES)

Workup

  1. temperatureThe RM was cooled to rt
  2. customcrystallized with diethylether
  3. filtrationThe suspension was filtered
  4. customthe cake was triturated again in hot EtOAc
  5. temperaturecooled after in the freezer
  6. filtrationThe suspension was filtered again
  7. washThe cake was washed with EtOAc
  8. customdried in the vacuum oven

Sources & evidence

ORD record
ord-1da2932a10a84824ab79bf75e06f29dd
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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