2,2,2-Trifluoroethanesulfonyl chloride → HCID 23521673, compound

HRID 392457Notes

Reaction equation

HRID 392457 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:9])=[CH:4][CH:3]=1.[F:18][C:19]([F:26])([F:25])[CH2:20][S:21](Cl)(=[O:23])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[S:21]([CH2:20][C:19]([F:26])([F:25])[F:18])(=[O:23])=[O:22])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 43182253HCID 43182253, compound

Product 1

HCID 23521673HCID 23521673, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(1-(4-bromophenyl)ethyl)pyrid-3-ylmethylamine (630 mg, 2.16 mmol) and 4-(dimethylamino)pyridine (263 mg, 2.16 mmol) in 18 ml of dichloromethane was treated with 2,2,2-trifluoroethylsulfonyl chloride (420 mg, 2.3 mmol) with stirring for 15 minutes at room temperature. The solution was concentrated to approximately 2 ml and directly purified by radial chromatography on a 1 micron silica plate, eluting with 3% methanol/dichloromethane. The fractions were concentrated to afford the title compound. 1H NMR: 8.52 (bs,1H), 8.42 (bs,1H), (d,1H,J=8 Hz), 7.45 (d,2H,J=8 Hz), 7.22 (d,2H,J=8 Hz), 5.25 (q,1H,J=8 Hz), 4.38 (q,2H,ABX), 3.6 (q,2H,J=12 Hz), 1.68 (d,3H,J=8 Hz). MS calcd. 437.3; MS (M+1),(M+2), 438.0,439.0.

Workup

  1. concentrationThe solution was concentrated to approximately 2 ml
  2. customdirectly purified by radial chromatography on a 1 micron silica plate
  3. washeluting with 3% methanol/dichloromethane
  4. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-18c6822837374ac9a680b1765e455d99
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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