Thionyl Chloride → HCID 67282943, compound

HRID 913024Notes

Reaction equation

HRID 913024 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[N:11]([CH3:22])[C:10]=1[CH2:23]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>C(#N)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[N:11]([CH3:22])[C:10]=1[CH2:23][Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67281599HCID 67281599, compound

Product 1

HCID 67282943HCID 67282943, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-benzyloxy-2-hydroxymethyl-1-methyl-6-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (0.31 g, 0.90 mmol) in acetonitrile (8 mL) was added thionyl chloride (0.33 mL, 4.5 mmol) at room temperature. A clear solution resulted. The reaction was completed in 10 min. The reaction mixture was evaporated to dryness to give crude 3-benzyloxy-2-chloromethyl-1-methyl-6-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as an oil. The crude oil obtained was taken up in ethanol (10 mL) to give a clear solution. To the solution was added sodium borohydride (380 mg, 10 mmol) in several portions. The reaction was completed within a few min. The reaction mixture was diluted with methanol. The resulting clear solution was evaporated to dryness to give a solid. The solid was repeatedly extracted with dichloromethane. The combined dichloromethane solutions were combined and evaporated to dryness. Purification of the residue by column chromatography on silica gel (methanol/dichloromethane, 5/100 to 8/100 v/v) afforded the title compound (0.20 g, 67% yield, HPLC Method 1 (Example 24), RT=14.4 min). 1H NMR (DMSO-d6+D2O) δ ppm: 7.36 (m, 5H), 6.53 (s, 1H), 5.50 (q, J=6.5 Hz, 1H), 5.00 (s, 2H), 3.56 (s, 3H), 2.24 (s, 3H).

Workup

  1. customA clear solution resulted
  2. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-ce384dbacb1044e1bc192f6d13b8746c
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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