Ether hydrochloride → Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)

HRID 1667350

反応式

HRID 1667350 の反応式
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[O:14])[N:8]=1)=[O:5].C(OCC)C.[ClH:33]>C(O)(C)C>[ClH:33].[F:27][C:22]1[CH:23]=[C:24]([F:26])[CH:25]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[O:14])[N:8]=1)=[O:5]

参加物

4

反応物 2

HCID 10953452Ether hydrochlorideHCID 11610526Lasmiditan

生成物 1

HCID 17980336Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)収率 93%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Dissolve 2,4,6-trifluoro-N-[6-(1-methylpiperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide-free base (5 g, 23.26 mmol) in isopropanol (50 mL) at room temperature and add a solution of 3.3 M diethylether/HCl (8 mL). Heat the reaction mixture under reflux for 30 minutes. Cool the reaction mixture to room temperature and agitate for 2 hrs. Filter the resulting white precipitate and rinse with isopropanol (5 mL). Dry the residual solid under reduce pressure at 40° C. overnight to obtain the title compound (5.12 g, 93% yield). M.p. 223-224° C. (sublimation); 1H NMR (400 MHz, d6-DMSO) d ppm 1.94 (m, 2H) 2.14 (m, J=11.15 Hz, 2H) 2.74 (s, 3H) 2.99 (m, J=9.19 Hz, 2H) 3.49 (m, J=11.15 Hz, 2H) 3.77 (m, 1H) 7.41 (t, J=8.71 Hz, 2H) 7.78 (d, J=7.43 Hz, 1H) 8.10 (t, J=7.92 Hz, 1H) 8.37 (d, J=6.85 Hz, 1H) 10.50 (s, 1H) 11.51 (s, 1H); 13C-NMR: (100.61 MHz, Chloroform-D) ppm 200.7; 130.6-158.0 (m, C-F-couplings); 150.4; 150.1; 140.2; 118.5; 118.2; 111.9; 101.3 (t, C-F couplings); 52.8; 42.6; 25.2

後処理

  1. temperatureHeat the reaction mixture
  2. temperatureunder reflux for 30 minutes
  3. filtrationFilter the resulting white precipitate
  4. washrinse with isopropanol (5 mL)
  5. customDry the residual solid
  6. customat 40° C.
  7. customovernight

出典と根拠

ORDレコード
ord-46b787f3f1c648b7b6f99d8b09e003eb
出典データセット
uspto-grants-2011_10
特許番号
US08044207B2

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