Water → 1-(3-Chloromethyl-4-methyl-pyridin-2-ylmethyl)-3-trifluoromethyl-1H-pyridin-2-one

HRID 1959606Notes

Reaction equation

HRID 1959606 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]2=[O:19])[C:3]=1[CH2:20]OC1CCCCO1.O=S(Cl)[Cl:30].O>C(Cl)Cl>[Cl:30][CH2:20][C:3]1[C:4]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]2=[O:19])=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 441901701-[4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-ylmethyl]-3-trifluoromethyl-1H-pyridin-2-one

Product 1

HCID 441910351-(3-Chloromethyl-4-methyl-pyridin-2-ylmethyl)-3-trifluoromethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-ylmethyl]-3-trifluoromethyl-1H-pyridin-2-one (100 mg. 0.26 mmol) was dissolved in DCM (5 mL). SOCl2 (97 μL. 1.31 mmol) and water (25 μL) were added and the reaction mixture was stirred for 1 h at RT. After removal of the solvents in vacuo the resulting title compound was used for the next reaction without purification. MS (m/z): 317.0 [M+H+].

Workup

  1. customAfter removal of the solvents in vacuo the resulting title compound
  2. customwas used for the next reaction without purification

Sources & evidence

ORD record
ord-81d04ae57011485fb17341405a273f0e
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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