Triethylamine → HCID 86617871, compound

HRID 2426796Notes

Reaction equation

HRID 2426796 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]([CH3:15])[CH2:10][CH:11]2[CH2:13][CH:12]2[CH3:14])[N:6]=[C:5]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])[CH:4]=1.C(N(CC)CC)C>ClCCl.CS(C)=O.CCOC(C)=O>[CH:2]([C:3]1[CH:8]=[C:7]([N:9]([CH3:15])[CH2:10][CH:11]2[CH2:13][CH:12]2[CH3:14])[N:6]=[C:5]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:18])=[O:19])[CH:4]=1)=[O:1]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 67252471HCID 67252471, compound

Product 1

HCID 86617871HCID 86617871, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-(hydroxymethyl)-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide (480 mg, 1.53 mmol) in dichloromethane (10 mL) and DMSO (2.5 mL) was added triethylamine (1.07 mL, 7.66 mmol) and SO3-pyridine (975 mg, 6.13 mmol). The reaction mixture was stirred at rt for 0.5 h, diluted with EtOAc, washed with 1N HCl, sat'd aq NaHCO3, brine, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica, 25-50% EtOAc/hexanes) to provide N-(4-formyl-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide. 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 6.92 (s, 1H), 6.72 (s, 1H), 3.53 (A of ABX, dd, J=14.8, 6.4 Hz, 1H), 3.40 (s, 3H), 3.36 (B of ABX, dd, J=14.8, 6.8 Hz, 1H), 3.15 (s, 3H), 3.13 (s, 3H), 1.04 (d, J=6.0 Hz, 3H), 0.78-0.62 (m, 2H), 0.45-0.37 (m, 1H), 0.31-0.24 (m, 1H).

Workup

  1. washwashed with 1N HCl
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica, 25-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-56cd8bc00a3c44bbbadb440bc21e87a5
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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