2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178516535、化合物

HRID 474746ノート

反応式

HRID 474746 の反応式
CS[C:3]1[NH:4][CH:5]=[CH:6][C:7](=[O:9])[N:8]=1.[Cl:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=2)=[CH:13][C:12]=1[C:27]([F:30])([F:29])[F:28]>N1C=CC=CC=1>[Cl:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][C:3]3[NH:4][CH:5]=[CH:6][C:7](=[O:9])[N:8]=3)=[CH:18][CH:17]=2)=[CH:13][C:12]=1[C:27]([F:28])([F:29])[F:30]

参加物

4

反応物 2

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178418670HCID 178418670、化合物

生成物 1

HCID 178516535HCID 178516535、化合物収率 77.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

2-Methylsulfanyl-1H-pyrimidin-4-one (70 mg, 0.492 mmol, 1.41 eq) and 2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (110 mg, 0.348 mmol, 1 eq) were heated in a sealed vial at 150° C. in 400 μl of dry pyridine for 16 hours. Solvent was then evaporated and the resulting crude was purified by chromatography on BIOTAGE SP1 purification device using 10 g normal phase silica SNAP column and DCM/30% MeOH in DCM solvent system (gradient 2-20% of 30% MeOH in DCM in 20 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and the resulting crude was triturated with diisopropyl ether and cyclohexane to afford 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1H-pyrimidin-4-one (111 mg, yield=73.8%, purity=95%) as a white powder. MS: [M+H]+=410.33 1H NMR (300 MHz; CDCl3) δ/ppm 2.92 (t, J=6.95 Hz, 2H), 3.61-3.72 (m, 2H), 5.59 (d, J=6.38 Hz, 1H), 6.18 (br.s, 1H), 6.95 (d, J=8.51 Hz, 2H), 7.03 (dd, J=9.07 Hz, J=2.69 Hz, 1H), 7.24 (d, J=8.51 Hz, 1H), 7.30 (d, J=2.69 Hz, 1H), 7.41 (d, J=8.80 Hz, 1H), 7.77 (d, J=6.38 Hz, 1H), 11.77 (br.s, 1H)

後処理

  1. customSolvent was then evaporated
  2. customthe resulting crude was purified by chromatography on BIOTAGE SP1 purification device
  3. customSolvent from the gathered fractions of appropriate composition was evaporated
  4. customthe resulting crude was triturated with diisopropyl ether and cyclohexane

出典と根拠

ORDレコード
ord-ea525f3c52bd47e6a25880ecd692631f
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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