Pyridine → HCID 59226230, compound

HRID 1621287Notes

Reaction equation

HRID 1621287 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1>ClCCl.N1C=CC=CC=1.ClCCl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]([CH2:7][CH:8]([O:9][CH3:10])[O:11][CH3:12])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

7

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chloride3×HCID 59226238HCID 59226238, compound

Product 1

HCID 59226230HCID 59226230, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Procedure

147.0 g (3-Chloro-4-fluoro-benzyl)-(2,2-dimethoxy-ethyl)-amine (54, crude product) were dissolved in 540 ml of dichloromethane/pyridine (8:1). At 0° C. a solution of 145.8 g (1.04 mol) p-toluenesulfonylchloride in 200 ml of dichloromethane was added. After 5 h at room temperature additional 20 ml of pyridine, 29.16 g (0.15 mol) p-toluene-sulfonylchloride and a catalytic amount of DMAP were added. The solution was stirred at room temperature for 7 h and then refluxed for additional 4 h. Again 29.16 g (0.15 mol) p-toluene-sulfonylchloride and a catalytic amount of DMAP were added and the mixture was stirred overnight. For workup, the solution was washed twice with 2 N HCl and twice with saturated NaHCO3-solution. The organic layer was dried with MgSO4 and evaporated. Final silicagel chromatography (heptane/ethyl acetate 4:1) gave 155 g of the title compound as a yellow oil. Rt=1.80 min (Method B). Detected mass: 370.2 (M-OMe−).

Workup

  1. temperaturerefluxed for additional 4 h
  2. stirringthe mixture was stirred overnight
  3. washFor workup, the solution was washed twice with 2 N HCl and twice with saturated NaHCO3-solution
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-22d48f4e4f7b4b46bf49fbe58268b9ec
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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