Ammonium Chloride → HCID 67252266, compound

HRID 2426808Notes

Reaction equation

HRID 2426808 reaction equation
[CH2:1]([N:8]([CH2:29][CH:30]1[CH2:32][CH:31]1[CH3:33])[C:9]1[CH:10]=[C:11]([CH:18]=[C:19]([N:21]([S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[CH3:22])[N:20]=1)[C:12](N(OC)C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][Mg]Br.[Cl-].[NH4+]>C1COCC1>[C:12]([C:11]1[CH:10]=[C:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:29][CH:30]2[CH2:32][CH:31]2[CH3:33])[N:20]=[C:19]([N:21]([CH3:22])[S:23]([CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:25])[CH:18]=1)(=[O:13])[CH3:34]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86617876HCID 86617876, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67252266HCID 67252266, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of 2-{benzyl[(2-methylcyclopropyl)methyl]amino}-6-[(isopropylsulfonyl)(methyl)amino]-N-methoxy-N-methylisonicotinamide (860 mg, 1.81 mmol) from Step A in 6 mL dry THF was added methylmagnesium bromide (3.62 mL, 10.8 mmol, 3M solution in diethyl ether). The reaction mixture was allowed to slowly warm to 0° C. over 1 h, at which time it was poured onto 20 mL of sat. ammonium chloride and extracted with ethyl acetate (3×30 mL). The combined organics were washed with brine (30 mL), dried over sodium sulfate, and concentrated. Purification by automated flash chromatography (silica gel cartridge, 0-100% ethyl acetate/hexanes over 35 minutes) afforded N-(4-acetyl-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylpropane-2-sulfonamide as a bright yellow solid. LCMS [M+H]=430.1.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combined organics were washed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by automated flash chromatography (silica gel cartridge, 0-100% ethyl acetate/hexanes over 35 minutes)

Sources & evidence

ORD record
ord-b96e73fc26fd466ca64634cdebd7e87c
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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