Pyridine → HCID 18440722, compound

HRID 457752Notes

Reaction equation

HRID 457752 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[S:10][C:9]([C:11]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](=[O:32])[N:17]([CH2:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[C:18]3=[O:23])=[O:12])=[CH:8][CH:7]=1.N1C=CC=CC=1>ClCCl.O>[C:1]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:25][CH2:24][N:17]2[C:16](=[O:32])[C:15]3[C:19](=[CH:20][CH:21]=[CH:22][C:14]=3[NH:13][C:11]([C:9]3[S:10][C:6]([Cl:5])=[CH:7][CH:8]=3)=[O:12])[C:18]2=[O:23])[CH2:27][CH2:28]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18440685HCID 18440685, compound

Product 1

HCID 18440722HCID 18440722, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent2×

Procedure

At room temperature, 17 μl (0.24 mmol) of acetyl chloride are added dropwise to a solution of 50 mg (0.12 mmol) of 5-chloro-N-{1,3-dioxo-2-[2-(4-piperidinyl)ethyl]-2,3-dihydro-1H-isoindol-4-yl}-2-thiophenecarboxamide and 0.1 ml of pyridine in 1 ml of absolute dichloromethane. After 1 h at room temperature, a few drops of water are added and the mixture is diluted with dichloromethane. The mixture is washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The crude product is purified by chromatography on silica gel (dichloromethane/methanol 98:2).

Workup

  1. washThe mixture is washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by chromatography on silica gel (dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-56b6b8132c5f4a97aa765fd2c881010d
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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