Hydrochloric Acid → 6-Amino-5-methyl-4-[(4-phenoxyphenyl)amino]pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796599Notes

Reaction equation

HRID 1796599 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10]([NH:13]C(=O)OCC3C=CC=CC=3)[C:11]([CH3:12])=[C:5]2[C:4]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)#[N:2].Cl>CO.[Pd]>[NH2:13][C:10]1[C:11]([CH3:12])=[C:5]2[C:4]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:29][CH:30]=3)=[C:3]([C:1]#[N:2])[CH:8]=[N:7][N:6]2[CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20791574[3-Cyano-5-methyl-4-[(4-phenoxyphenyl)amino]pyrrolo[1,2-b]pyridazin-6-yl]carbamic Acid, Phenylmethyl Ester

Product 1

HCID 221794886-Amino-5-methyl-4-[(4-phenoxyphenyl)amino]pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 109.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 11A (40 mg, 0.082 mmol) in MeOH (4 mL) was added Pd/C (12 mg), and the reaction mixture was stirred under hydrogen (1 atm) for 30 minutes, after which time HCl (4M in dioxane, 0.1 mL) was added. The reaction mixture was filtered and the filtrate concentrated in vacuo to provide 32 mg of compound 11B as an orange solid (quantitative yield as HCl salt). HPLC: 100% at 2.90 min (retention time) (YMC S5 ODS column, 4.6×50 mm eluting with 10-90% McOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm). MS (ES): m/z 356.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3d8ca560439c4677a8be8e8ccfadc6ae
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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