Ammonium Hydroxide → HCID 59651097, compound

HRID 2426798Notes

Reaction equation

HRID 2426798 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[C:11]([CH:13]2[CH2:15][O:14]2)[CH:10]=[C:9]([N:16]([CH3:22])[CH2:17][CH:18]2[CH2:20][CH:19]2[CH3:21])[N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].[NH4+:23].[OH-]>CCO>[NH2:23][CH2:15][CH:13]([C:11]1[CH:10]=[C:9]([N:16]([CH3:22])[CH2:17][CH:18]2[CH2:20][CH:19]2[CH3:21])[N:8]=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:12]=1)[OH:14]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86617872HCID 86617872, compound

Product 1

HCID 59651097HCID 59651097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(4-formyl-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide (435 mg, 1.40 mmol) in acetonitrile (5 mL) was added 5 drops water, trimethylsulfonium iodide (342 mg, 1.68 mmol) and potassium hydroxide (188 mg, 3.35 mmol). The reaction was stirred at 65° C., sealed, for 3 h, diluted with EtOAc, washed with sat'd aq NaHCO3, brine, dried over sodium sulfate, and concentrated in vacuo to provide N-methyl-N-(6-{methyl[(2-methylcyclopropyl)methyl]amino}-4-oxiran-2-ylpyridin-2-yl)methanesulfonamide, used as is in the next step. A solution of N-methyl-N-(6-{methyl[(2-methylcyclopropyl)methyl]amino}-4-oxiran-2-ylpyridin-2-yl)methanesulfonamide (440 mg, 1.35 mmol) in EtOH (10 mL) and NH4OH (15 mL) was stirred at 60° C., sealed, for 16 h, concentrated in vacuo and purified by flash chromatography (silica, 5-15% (10% NOH/MeOH)/CH2Cl2) to provide N-(4-(2-amino-1-hydroxyethyl)-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide as a thick oil. 1H NMR (400 MHz, CD3OD) δ 6.52 (s, 1H), 6.47 (s, 1H), 4.58 (X′ of A′B′X′, dd, J=7.6, 4.0 Hz, 2H), 3.54 (A of ABX, dd, J=14.4, 6.4 Hz, 1H), 3.35 (B of ABX, dd, J=14.4, 6.8 Hz, 1H), 3.30 (s, 3H), 3.13 (s, 3H), 3.08 (s, 3H), 3.86 (A′ of A′B′X′, dd, J=13.2, 4.0 Hz, 1H), 2.76 (B′ of A′B′X′, dd, J=13.2, 7.6 Hz, 1H), 1.02 (d, J=6.0 Hz, 3H), 0.80-0.65 (m, 2H), 0.46-0.39 (m, 1H), 0.25-0.18 (m, 1H).

Workup

  1. customsealed, for 16 h
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography (silica, 5-15% (10% NOH/MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-29d589c6abc84e818ff3e92e7262c540
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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