Diisopropylethylamine → HCID 68582528, compound

HRID 2233971Notes

Reaction equation

HRID 2233971 reaction equation
Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=2)[N:23]=[C:22]([C:31]([O:33][CH3:34])=[O:32])[CH:21]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[Cl:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([C:31]([O:33][CH3:34])=[O:32])[CH:21]=[C:20]2[N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:10]([C:4]2[NH:5][C:6]([CH3:9])=[C:7]([Cl:8])[C:3]=2[Cl:2])=[O:11])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 29923271Methyl 4,6-dichloroquinoline-2-carboxylateHCID 68579996HCID 68579996, compound2×

Product 1

HCID 68582528HCID 68582528, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1; 59 mg, 0.21 mmol), methyl 4,6-dichloroquinoline-2-carboxylate (F R Alexandre, et. al., Tetrahedron 2003, 59: 1413; 57 mg 0.22 mmol) and diisopropylethylamine (0.10 ml) in DMF (2.0 ml) was heated in a microwave reactor to 180° C. for 30 minutes. The reaction was diluted with 50 ml of EtOAc, then extracted with 25 ml of 1 N NaOH, 2×25 ml of water, dried over anhydrous MgSO4 and concentrated in vacuo. The crude solid was flash chromatographed through neutral silica gel using EtOAc as the eluent to give 37 mg of the title compound; crystallization from MeOH gave a white solid.

Workup

  1. extractionextracted with 25 ml of 1 N NaOH, 2×25 ml of water
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customchromatographed through neutral silica gel

Sources & evidence

ORD record
ord-b0cb4fbd33f2403a9d5ab77a16c22fe5
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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