2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178432724, 화합물

HRID 474876

반응식

HRID 474876 반응식
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[N:11]=[C:12](SC)[NH:13][CH:14]=2)=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=2)=[CH:21][C:20]=1[C:35]([F:38])([F:37])[F:36]>C(O)C>[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][C:12]3[NH:13][CH:14]=[C:9]([CH2:8][C:5]4[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=4)[C:10](=[O:17])[N:11]=3)=[CH:26][CH:25]=2)=[CH:21][C:20]=1[C:35]([F:36])([F:37])[F:38]

참가 물질

4

반응물 2

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178503542HCID 178503542, 화합물

생성물 1

HCID 178432724HCID 178432724, 화합물수율 69.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5-(2-Methyl-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (30 mg, 248.31 gmol−1, 0.12 mmol, 1 eq) and 2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (57 mg, 315.73 gmol−1 0.18 mmol, 1.5 eq) were stirred in 300 μl of absolute ethanol at 125° C. for 50 hours. Solvent from the reaction mixture was evaporated and the resulting crude was purified by preparative HPLC-MS. The gathered fractions of appropriate composition were lyophilized and the resulting oily product was triturated with DCM and diethyl ether to afford 2-{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-(2-methyl-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (43 mg, yield=65.5%, purity=95%) MS: [M+H]+=516.38. 1H NMR (300 MHz; CDCl3) δ/ppm 2.64 (s, 3H), 2.89 (t, J=7.0 Hz, 2H), 3.52 (s, 2H), 3.57-3.66 (m, 2H), 5.20 (br.s., 1H), 6.94 (d, J=7.75 Hz, 2H), 7.02 (d, J=9.26 Hz, 1H), 7.17-7.30 (m, 3H), 7.39 (d, J=8.70 Hz, 1H), 7.67 (s, 1H), 8.49 (s, 2H), 12.18 (br.s., 1H).

후처리

  1. customSolvent from the reaction mixture was evaporated
  2. customthe resulting crude was purified by preparative HPLC-MS
  3. customthe resulting oily product was triturated with DCM and diethyl ether

출처 및 근거

ORD 기록
ord-36fcbb48921847c191fe3bc5b4a17faa
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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