Ethanol → HCID 22112748, compound

HRID 564754Notes

Reaction equation

HRID 564754 reaction equation
C([O:3][C:4]([C:6]1[C:11]2=[CH:12][S:13][C:14]([NH2:15])=[C:10]2[C:9](=O)[N:8]([C:17]2[CH:22]=[CH:21][C:20](OC)=[CH:19][CH:18]=2)[N:7]=1)=[O:5])C.[OH-:25].[Na+].[CH2:27]([OH:29])C>O>[NH2:15][C:14]1[S:13][CH:12]=[C:11]2[C:10]=1[C:9](=[O:25])[N:8]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([O:29][CH3:27])[CH:22]=1)[N:7]=[C:6]2[C:4]([OH:3])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 719449HCID 719449, compound

Product 1

HCID 22112748HCID 22112748, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 5-amino-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester (3 g, 8.69 mmol, prepared in example 23) in a mixture of ethanol (50 ml) and water (25 ml) was added sodium hydroxide (0.38 g, 9.55 mmol). The resulting reaction mixture was stirred for 2.5 h at room temperature. Water (150 ml) was added, undissolved matter was filtered off. The aqueous phase was washed with diethyl ether (2×100 ml), pH was adjusted to pH=4 by addition of concentrated hydrochloric acid. The precipitate was filtered off and washed with water (2×50 ml), heptane (2×50 ml) and dried in vacuo at 50° C. for 18 h affording 2.3 g (83%) of the title compound as a solid.

Workup

  1. customThe resulting reaction mixture
  2. filtrationundissolved matter was filtered off
  3. washThe aqueous phase was washed with diethyl ether (2×100 ml)
  4. additionpH was adjusted to pH=4 by addition of concentrated hydrochloric acid
  5. filtrationThe precipitate was filtered off
  6. washwashed with water (2×50 ml), heptane (2×50 ml)
  7. customdried in vacuo at 50° C. for 18 h

Sources & evidence

ORD record
ord-aa358d32785c42ffb475801849c5fa6c
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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