3-Pyridinemethanol → HCID 21186293, compound

HRID 1384237Notes

Reaction equation

HRID 1384237 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.[H][H].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:26]([S:27]([N:30](C(OCC(C)C)=O)[C:31]3[C:36]([O:37][CH3:38])=[N:35][C:34]([CH3:39])=[CH:33][N:32]=3)(=[O:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1>C1COCC1>[CH3:14][CH2:15][O:10][CH2:9][CH3:5].[CH3:38][O:37][C:36]1[C:31]([NH:30][S:27]([C:26]2[C:21]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][O:10][CH2:9][C:5]4[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=4)=[CH:20][CH:19]=3)=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:29])=[O:28])=[N:32][CH:33]=[C:34]([CH3:39])[N:35]=1

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 211862832-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21186293HCID 21186293, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oil-free sodium hydride (240 mg) was added to a stirred solution of 3-pyridyl carbinol (1.09 g) in dry THF (20 ml). When evolution of hydrogen ceased, 2-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (549 mg) was added and the mixture was stirred for 2 hours. Volatile material was removed by evaporation and saturated ammonium chloride solution (10 ml) was added to the residue. The mixture was extracted with ethyl acetate (3×20 ml) and the extracts were dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/ethyl acetate (1:19 v/v), to give after trituration with ether N-(3-methoxy-5-methylpyrazin-2-yl)-2-{4-[(3-pyridyl)methoxymethyl]phenyl}pyridine-3-sulphonamide (187 mg), m.p. 183-185° C.; microanalysis found: C, 60.9; H, 4.9; N, 14.2%; C24H23N5O4S requires: C, 60.4; H, 4.85; N, 14.7%.

Workup

  1. customVolatile material was removed by evaporation and saturated ammonium chloride solution (10 ml)
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  4. dry with materialthe extracts were dried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by flash chromatography
  7. washeluting with methanol/ethyl acetate (1:19 v/v)

Sources & evidence

ORD record
ord-be6a386df08b4e4aa36119e74a8af1f7
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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