Hydrochloric Acid → 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid

HRID 1796649Notes

Reaction equation

HRID 1796649 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[N:11]=[CH:12][C:13]([C:29]#[N:30])=[C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:9]2=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>CCO>[C:29]([C:13]1[CH:12]=[N:11][N:10]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=[C:9]2[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)#[N:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 210250973-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid ethyl ester

Product 1

HCID 221796343-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 406 (15.6 mg, 0.039 mmol) and 1N NaOH (150 μl, 0.15 mmol) in EtOH (5 ml) was stirred at 50-70° C. for 15 h. 1N HCl (150 μl, 0.15 mmol) was added, solvent was removed, and the residue was purified by preparative TLC to give the title compound (14.1 mg, 98%) as a tan solid. LCMS Found: (M+H)+=371.1

Workup

  1. customsolvent was removed
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-52471633d3dd443b9554316070f0978e
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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