Diisopropylethylamine → HCID 68582528, 화합물

HRID 2233971노트

반응식

HRID 2233971 반응식
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

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 29923271Methyl 4,6-dichloroquinoline-2-carboxylateHCID 68579996HCID 68579996, 화합물2회

생성물 1

HCID 68582528HCID 68582528, 화합물수율 35.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b0cb4fbd33f2403a9d5ab77a16c22fe5
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

반응 노트

불러오는 중…