Water → 6-[Methyl(3,3,3-trifluoropropyl)carbamoyl]nicotinic acid

HRID 1099439노트

반응식

HRID 1099439 반응식
[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=1)=[O:7].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH3:22][N:5]([CH2:4][CH2:3][C:2]([F:19])([F:18])[F:1])[C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1)=[O:7]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59354919HCID 59354919, 화합물

생성물 1

HCID 593549166-[Methyl(3,3,3-trifluoropropyl)carbamoyl]nicotinic acid수율 47.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 6-[(3,3,3-trifluoropropyl)carbamoyl]nicotinate (2.4 g, 8.6 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% suspension in mineral oil) (1.3 g). The reaction mixture was stirred at ambient temperature for 1 h. Methyl iodide (3.42 g, 5.0 mL, 24.1 mmol) was added and the reaction mixture was stirred over night and then added water (20 mL). The reaction mixture was stirred for another 30 min and then extracted with ethyl acetate (2×50 mL). The aqueous layer was acidified with citric acid and the formed precipitate was filtered off and dried in vacuum oven to yield 1.12 g (47%) of the title compound; 1H NMR (400 MHz, CDCl3) δ ppm 9.26 (d, 1 H), 8.49 (d, 1 H), 7.78-7.91 (dd, 1 H), 3.80 (t, 1 H), 3.61-3.73 (m, 1 H), 3.16 (d, 3 H), 2.46-2.76 (m, 2 H); MS (ESI) m/z 277[M+H+].

후처리

  1. stirringthe reaction mixture was stirred over night
  2. stirringThe reaction mixture was stirred for another 30 min
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. filtrationthe formed precipitate was filtered off
  5. customdried in vacuum oven

출처 및 근거

ORD 기록
ord-73b45ad9e93b4a22a8e546b3768918bd
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143408B2

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