Ethoxyacetyl chloride → 1-[2-(Ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-ol

HRID 352008Notes

Reaction equation

HRID 352008 reaction equation
[NH2:1][C:2]1[C:3]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4][C:5]([CH3:15])=[C:6]([CH3:14])[C:7]=1[NH:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11].[CH2:23]([O:25][CH2:26][C:27](Cl)=O)[CH3:24]>N1C=CC=CC=1>[CH2:23]([O:25][CH2:26][C:27]1[N:8]([CH2:9][C:10]([CH3:11])([OH:12])[CH3:13])[C:7]2[C:6]([CH3:14])=[C:5]([CH3:15])[N:4]=[C:3]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:2]=2[N:1]=1)[CH3:24]

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 129912021-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 103844701-[2-(Ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To the product from Part F (1-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-ylamino]-2-methylpropan-2-ol was added 10 ml of pyridine. Ethoxyacetyl chloride (3.014 g) was added dropwise to the resulting mixture. The resulting solution was brought to reflux for about 3 days with an intervening day of cooling at about 5° C. The solvent was removed under reduced pressure, and the resulting product dissolved in ethyl acetate containing sodium bicarbonate. The resulting mixture was extracted with water. The resulting organic layer was dried with magnesium sulfate, the solvent was removed under reduced pressure, and the product was cooled to about 5° C. The resulting solid was recrystallized from ethyl acetate. The supernatant was concentrated under reduced pressure to the point of crystallization. This was repeated, resulting in a total of three fractions of crystals in the amounts of 1.500 g, 2.370 g, and 1.527 g, respectively.

Workup

  1. temperatureto reflux for about 3 days with an intervening day
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe resulting product dissolved in ethyl acetate
  4. additioncontaining sodium bicarbonate
  5. extractionThe resulting mixture was extracted with water
  6. dry with materialThe resulting organic layer was dried with magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. temperaturethe product was cooled to about 5° C
  9. customThe resulting solid was recrystallized from ethyl acetate
  10. concentrationThe supernatant was concentrated under reduced pressure to the point of crystallization
  11. customresulting in a total of three fractions of crystals in the amounts of 1.500 g, 2.370 g, and 1.527 g

Sources & evidence

ORD record
ord-9a5a40afda5644558a3200e2948891a6
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Reaction notes

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