Hydrochloric Acid → 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid

HRID 1796670Notes

Reaction equation

HRID 1796670 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:32])=[C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21][C:22]4[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=4)=[C:17]([Cl:28])[CH:16]=3)=[C:12]([C:29]#[N:30])[CH:11]=[N:10][N:9]2[CH:31]=1)=[O:5])C.[OH-].[Na+].CCO.C1COCC1.Cl>CCOC(C)=O>[Cl:28][C:17]1[CH:16]=[C:15]([NH:14][C:13]2[C:8]3[N:9]([CH:31]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=3[CH3:32])[N:10]=[CH:11][C:12]=2[C:29]#[N:30])[CH:20]=[CH:19][C:18]=1[S:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21025108HCID 21025108, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 221794404-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 426 (70 mg, 0.15 mmol) and 6N NaOH (2 ml, 1.0 mmol) in a mixed solvents of EtOH/THF (2/1) (3 ml) was stirred at rt for 2 days. Neutralized with concentrated HCl to PH=6, treated with EtOAc (50 ml), the mixture was washed with H2O (2×20 ml) and brine (20 ml), dried with Na2SO4. Removal of the solvent gave 428A (55 mg, 93%) as a yellow solid. The product was used in next step without further purification. It has a retention time of 4.73 min (standard LC1 method, 8 min run). MS Found: (M+H)+=439.1

Workup

  1. washthe mixture was washed with H2O (2×20 ml) and brine (20 ml)
  2. dry with materialdried with Na2SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-1347c6a9aba7446f9996aba5aae09645
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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