Diisopropylethylamine → HCID 68582528、化合物

HRID 2233971ノート

反応式

HRID 2233971 の反応式
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

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 29923271Methyl 4,6-dichloroquinoline-2-carboxylateHCID 68579996HCID 68579996、化合物2 回

生成物 1

HCID 68582528HCID 68582528、化合物収率 35.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0cb4fbd33f2403a9d5ab77a16c22fe5
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

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