2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine → HCID 178432722, 화합물

HRID 474884노트

반응식

HRID 474884 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[CH3:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][C:29]2[C:30](=[O:37])[N:31]=[C:32](SC)[NH:33][CH:34]=2)=[CH:24][N:23]=1>C(O)C>[CH3:21][C:22]1[N:23]=[CH:24][C:25]([CH2:28][C:29]2[C:30](=[O:37])[N:31]=[C:32]([NH:18][CH2:17][CH2:16][C:13]3[CH:14]=[CH:15][C:10]([O:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:8][N:7]=4)=[CH:11][CH:12]=3)[NH:33][CH:34]=2)=[CH:26][N:27]=1

참가 물질

4

반응물 2

HCID 167707892-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamineHCID 178503542HCID 178503542, 화합물

생성물 1

HCID 178432722HCID 178432722, 화합물수율 19.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
125 °C

실험 절차

2-[4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethylamine (0.354 mmol, 1 eq) and 5-(2-methyl-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.322 mmol, 0.9 eq) were dissolved in dry ethanol (300 μL) and stirred at 125° C. for 50 hours. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of MeOH in DCM: 0-10% in 25CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 5-(2-methyl-pyrimidin-5-ylmethyl)-2-{2-[4-(5-trifluoromethyl-pyridin-2-yloxy)phenyl]ethylamino}-1H-pyrimidin-4-one (0.064 mmol, yield: 18%, HPLC-MS/UV:[M+H]+=483.37; rt: 0.89 mins; purity: 93%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.66 (s, 3H), 2.93 (t, J=7.39, 2H), 3.54 (s, 2H), 3.60-3.70 (m, 2H), 5.39 (br.s., 1H), 7.01 (d, J=8.69, 1H), 7.08 (d, J=8.50 2H), 7.27-7.31 (m, 2H), 7.66 (s, 1H), 7.89 (dd, J=9.58, J=2.73, 1H), 8.36-8.42 (m, 1H), 8.51 (s, 2H), 11.21 (br.s., 1H)

후처리

  1. customSolvent was evaporated
  2. customcrude product was purified on Biotage SP1 Snap Si 10
  3. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a5216c504f0c46df8abd70873c55ea61
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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