Ethyl Acetate → HCID 67452632, compound

HRID 869147Notes

Reaction equation

HRID 869147 reaction equation
[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17](C(OC)=O)=[CH:16][CH:15]=3)[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:24][Mg+].[Br-].CCO[C:30]([CH3:32])=[O:31].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[C:3]([C:8]2([CH2:12][NH:13][C:14]3[N:19]=[N:18][C:17]([C:30]([OH:31])([CH3:32])[CH3:24])=[CH:16][CH:15]=3)[CH2:9][CH2:10][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67451838HCID 67451838, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 67452632HCID 67452632, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A portion of the isolated methyl 6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazine-3-carboxylate (99 mg, 0.3 mmol, 1.0 equiv) was dissolved in THF (10 mL) and transferred to a 20 dram vial. The mixture was cooled to 0° C. and MeMgBr (3M in Et2O, 0.5 mL, 1.5 mmol, 5 equiv) was added. The reaction was allowed to warm to rt and then stirred for 15 min. The reaction mixture was poured into a mixture of EtOAc (30 mL) and saturated ammonium chloride (15 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography (0-20% MeOH/CH2Cl2) to give 42 mg (43%) of 2-(6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)propan-2-ol as a white powder. m/z=317 [M+H]+.

Workup

  1. temperatureto warm to rt
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid that
  7. customwas purified by silica gel column chromatography (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-37cd18e40b5c425bb198f4d58a84d13f
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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