Water → HCID 86661723、化合物

HRID 1020814ノート

反応式

HRID 1020814 の反応式
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]

参加物

6

反応物 4

HCID 962WaterHCID 10582773HCID 10582773、化合物HCID 537509302,5,6-Trichloropyridine-3-carboxamideHCID 178418922HCID 178418922、化合物

生成物 1

HCID 86661723HCID 86661723、化合物収率 87.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e88578d948a344f78c0cd0c7bc435f42
出典データセット
uspto-grants-2014_05
特許番号
US08716478B2

反応ノート

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