Ethyl 2-ethoxycarbonyl-3-(4-methoxy-3-thienylamino)prop-2-enoate → 3-Methoxy-6-ethoxycarbonylthieno[3,2-b]pyridin-7-(4H)-one

HRID 2107622Notes

Reaction equation

HRID 2107622 reaction equation
C(O[C:4]([C:6](=[CH:12][NH:13][C:14]1[C:18]([O:19][CH3:20])=[CH:17][S:16][CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:20][O:19][C:18]1[C:14]2[NH:13][CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4](=[O:5])[C:15]=2[S:16][CH:17]=1

Participants

3

Reactant 1

HCID 23046153Ethyl 2-ethoxycarbonyl-3-(4-methoxy-3-thienylamino)prop-2-enoate

Product 1

HCID 230461573-Methoxy-6-ethoxycarbonylthieno[3,2-b]pyridin-7-(4H)-one

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

To a refluxing solution of diphenyl ether (250 ml) was added ethyl 2-ethoxycarbonyl-3-(4-methoxy-3-thienylamino)prop-2-enoate (25 g, 0.0836 mol) portionwise. On completion of the addition, refluxing was continued for a further 20 minutes. The reaction mixture was allowed to cool and then diluted with petroleum ether (b.p. 40°-60°) (400 ml) to give a dark brown solid. This was collected by filtration, washed with petroleum-ether (b.p. 40°-60°) (100 ml) and dried. The solid was recrystallized from DMF (30 ml) to give the title compound as a pale purple solid, 12.7 g, m.p. 244°-247°.

Workup

  1. additionOn completion of the addition
  2. temperaturerefluxing
  3. temperatureto cool
  4. customto give a dark brown solid
  5. filtrationThis was collected by filtration
  6. washwashed with petroleum-ether (b.p. 40°-60°) (100 ml)
  7. customdried
  8. customThe solid was recrystallized from DMF (30 ml)

Sources & evidence

ORD record
ord-b80f8fbaf67e4cdd8110d129a95503c8
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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