Triethylamine → 2-[1-(dimethylamino)-2,2,2-trifluoroethyl]-3-hydroxy-1-methylpyridin-4(1H)-one

HRID 1519039노트

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HRID 1519039 반응식
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH:10](O)[C:11]([F:14])([F:13])[F:12].Cl.[CH3:17][NH:18][CH3:19].CCN(CC)CC>C(#N)C>[CH3:17][N:18]([CH3:19])[CH:10]([C:3]1[N:4]([CH3:9])[CH:5]=[CH:6][C:7](=[O:8])[C:2]=1[OH:1])[C:11]([F:14])([F:13])[F:12]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 67282261HCID 67282261, 화합물

생성물 1

HCID 498698882-[1-(dimethylamino)-2,2,2-trifluoroethyl]-3-hydroxy-1-methylpyridin-4(1H)-one수율 32%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a suspension of 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (5.00 g, 22.4 mmol) in 40 mL of acetonitrile at ice-water bath was added Vilsmeier's reagent (4.30 g, 33.6 mmol) portionwise. The resulting mixture was stirred for 2 h before being added to a suspension of dimethylamine hydrochloride (6.00 g, 73.6 mmol) and Et3N (15.0 mL, 107.6 mmol) in 30 mL of acetonitrile. The resulting suspension was stirred at RT for overnight. The solid was filtered off and the filtrate was concentrated to dryness. The residue was purified by flash chromatography on silica gel (10% MeOH in EtOAc as eluant) to afford title compound, Apo7041 (1.8 g). Yield=32%; 1H NMR (90 MHz, CD3OD-D4) δ (ppm): 7.63 (d, J=7.3 Hz, 1H), 6.41 (d, J=7.3 Hz, 1H), 4.78 (q, J=8.1 Hz, 1H), 3.99 (s, 3H), 2.41 (s, 6H); MS m/z 273 [M+Na]+, 251 [M+1]+, 206 (100%).

후처리

  1. stirringThe resulting suspension was stirred at RT for overnight
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by flash chromatography on silica gel (10% MeOH in EtOAc as eluant)

출처 및 근거

ORD 기록
ord-e8d84901ba164be8b936534c4b7d57fe
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073865B2

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