Water → 6-Chloro-4-(5-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-pyridin-2-ylamino)-2-methyl-2H-pyridazin-3-one

HRID 1431148Notes

Reaction equation

HRID 1431148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=O)OC(C)(C)C)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.O>C(O)=O.C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[CH3:19])=[CH:15][N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 68062453tert-Butyl (6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)methyl(2-methoxyethyl)carbamate

Product 1

HCID 667422656-Chloro-4-(5-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-pyridin-2-ylamino)-2-methyl-2H-pyridazin-3-oneYield 67.3%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Conditions

Temperature
70 °C

Procedure

tert-Butyl (6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)methyl(2-methoxyethyl)carbamate (95 mg, 0.22 mmol) was dissolved in 0.75 ml of formic acid and 1.4 ml of formalin. The reaction was heated at 70° C. for 4 hours. The reaction was cooled to room temperature, water was added and the aqueous layer was extracted with DCM. The aqueous layer was carefully basified with solid potassium carbonate and extracted 3 times with DCM. The crude product was purified by chromatography using a gradient of 5% to 15% methanol in DCM to give 50 mg (66.0%) of a white powder.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe aqueous layer was extracted with DCM
  3. extractionextracted 3 times with DCM
  4. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-904449ca6d6949d6bf7654200670096b
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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