Water → HCID 86661723, 화합물

HRID 1020814노트

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HRID 1020814 반응식
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:13][CH2:14][CH2:15][CH2:16][C:17]1([OH:20])[CH2:19][CH2:18]1.C(O[K])(C)(C)C.O>CN(C=O)C>[Cl:12][C:8]1[C:9]([Cl:11])=[N:10][C:2]([O:13][CH2:14][CH2:15][CH2:16][C:17]2([OH:20])[CH2:19][CH2:18]2)=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 10582773HCID 10582773, 화합물HCID 537509302,5,6-Trichloropyridine-3-carboxamideHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 86661723HCID 86661723, 화합물수율 87.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of compound 2,5,6-trichloronicotinamide (0.6 g, 2.7 mmol), 1-(3-hydroxypropyl)cyclopropanol (370 mg, 3.2 mmol) and tert-BuOK (363 mg, 3.2 mmol) in DMF was stirred at room temperature overnight and the reaction mixture was then poured into cold water, the mixture was extracted twice with ethyl acetate, the combined organic layers were washed with brine twice, dried over Na2SO4 and concentrated, the residue was purified by column chromatography (silica gel, Petroleum ether:EtOAc=1:0 to 5:1) to give the 5,6-dichloro-2-(3-(1-hydroxycyclopropyl)propoxy)nicotinamide (0.72 g, 73%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.65 (s, 1H), 8.29 (s, 1H), 8.03 (s, 1H), 5.48 (s, 1H), 4.82 (t, 2H, J=6.4 Hz), 2.36 (m, 2H), 1.97 (m, 2H), 0.94 (t, 2H), 0.73 (t, 2H).

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washthe combined organic layers were washed with brine twice
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (silica gel, Petroleum ether:EtOAc=1:0 to 5:1)

출처 및 근거

ORD 기록
ord-e88578d948a344f78c0cd0c7bc435f42
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716478B2

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