Pyridine → HCID 18440729, compound

HRID 457758Notes

Reaction equation

HRID 457758 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][N:14]([CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)[C:15]2=[O:20].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C1COCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][N:14]([CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:15]3=[O:20])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 18440731HCID 18440731, compound

Product 1

HCID 18440729HCID 18440729, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 0.97 g (5.35 mmol) of 5-chlorothiophene-2-carbonyl chloride is added dropwise to a suspension of 1.48 g (4.12 mmol) of tert-butyl 4-[2-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-piperidinecarboxylate, 1.7 ml (20.6 mmol) of pyridine and 25 mg (0.206 mmol) of 4-DMAP in 21 ml of absolute THF. The mixture is slowly warmed to room temperature and stirred overnight. The reaction 10 mixture is concentrated and then separated by chromatography on silica gel (dichloromethane/methanol 97:3).

Workup

  1. customThe reaction 10 mixture
  2. concentrationis concentrated
  3. customseparated by chromatography on silica gel (dichloromethane/methanol 97:3)

Sources & evidence

ORD record
ord-5602b2d43d844785849e684ca57a4a8e
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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