Hydrochloric Acid → 3-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid

HRID 2234131Notes

Reaction equation

HRID 2234131 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:18]=[N:17][C:16]=1[O:27]C)=[C:9]2[C:29]1[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH3:34][N:32]1[CH:33]=[C:29]([C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=3)[NH:11][C:10]=2[C:15]2[C:16](=[O:27])[NH:17][N:18]=[C:19]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[CH:20]=2)[CH:30]=[N:31]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 686385172-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-indole-5-carboxylic acid ethyl ester

Product 1

HCID 1359618733-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

350 mg of 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-indole-5-carboxylic acid ethyl ester is dissolved in 4 ml ethanol and 4 ml aqueous 2N NaOH and heated by microwave irradiation for 10 min at 150° C. The solution is neutralized with aqueous HCl and the product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 39 mg. LC-MS (ES+) 413 (M+H)+.

Workup

  1. customthe product is purified by preparative RP-HPLC
  2. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c3f1a7ac690d4d90b358691b612d4587
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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