Sodium Hydroxide → 3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid

HRID 1796676Notes

Reaction equation

HRID 1796676 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH3:32])=[C:7]2[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[CH:16][CH:15]=3)=[C:11]([C:29]#[N:30])[CH:10]=[N:9][N:8]2[CH:31]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:29]([C:11]1[CH:10]=[N:9][N:8]2[CH:31]=[C:5]([C:3]([OH:4])=[O:2])[C:6]([CH3:32])=[C:7]2[C:12]=1[NH:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[CH:18][CH:19]=1)#[N:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 210251483-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester

Product 1

HCID 221796673-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 430C (1.60 g, 3.73 mmol) and 6N NaOH (5 ml, 30 mmol) in a mixed solvent of MeOH/THF (20 ml, 1/1) was heated at reflux for 2 h, cooled to rt. Removed half of the solvent in vacuo. The residue was treated with H2O (30 ml), washed with CH2Cl2 (3×50 ml). The aqueous layer was acidified to PH=5 and extracted with EtOAc (3×50 ml). The combined organic layers were washed with H2O (2×30 ml) and brine (30 ml), dried with Na2SO4. Removal of the solvent under reduced pressure gave 430D (1.47 g, 95%) as a yellow powder. It has retention time of 5.88 min (∠Cl, 8 min. run). MS Found: (M+H)+=415.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customRemoved half of the solvent in vacuo
  4. additionThe residue was treated with H2O (30 ml)
  5. washwashed with CH2Cl2 (3×50 ml)
  6. extractionextracted with EtOAc (3×50 ml)
  7. washThe combined organic layers were washed with H2O (2×30 ml) and brine (30 ml)
  8. dry with materialdried with Na2SO4
  9. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-94a7c8d1793547359e124819b258ab42
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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