2-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanamine hydrochloride → HCID 178490000, 화합물

HRID 1627305노트

반응식

HRID 1627305 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([S:24][CH2:25][C:26]3[C:35]([F:36])=[CH:34][C:29]([O:30][CH2:31][CH2:32][NH2:33])=[CH:28][C:27]=3[F:37])=[N:14][CH:13]=2)([CH3:11])[CH3:10])=[CH:5][C:4]=1[O:38][CH3:39].[N-:40]([C:43]#[N:44])[C:41]#[N:42]>C(O)(C)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15]([S:24][CH2:25][C:26]3[C:27]([F:37])=[CH:28][C:29]([O:30][CH2:31][CH2:32][NH:33]/[C:43](/[NH2:44])=[N:40]/[C:41]#[N:42])=[CH:34][C:35]=3[F:36])=[N:14][CH:13]=2)([CH3:11])[CH3:10])=[CH:5][C:4]=1[O:38][CH3:39]

참가 물질

4

반응물 2

HCID 667399852-(4-((5-(2-(4-Chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanamine hydrochlorideHCID 178512229HCID 178512229, 화합물

생성물 1

HCID 178490000HCID 178490000, 화합물수율 57.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a solution of 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanamine hydrochloride (100 mg, 0.167 mmol) in isopropylalcohol (5 mL) was added dicyanamide (19.3 mg, 0.217 mmol) and the reaction mixture was heated at reflux for 24 h. Solvent was evaporated in vacuo and the residue was purified by column chromatography (CH2Cl2/MeOH=20:1) to give the title compound (60 mg, 57%) as an ivory solid. 1H NMR (400 MHz, CD3OD) δ 7.22 (s, 1H), 7.17 (d, J=8.2 Hz, 1H), 6.77 (t, J=8.43 Hz, 2H), 6.60-6.42 (m, 5H), 6.25 (dd, J=7.8, 4.7 Hz, 2H), 4.02 (t, J=4.54 Hz, 2H), 3.83 (s, 2H), 3.71 (s, 3H), 3.56 (t, J=4.65 Hz, 2H), 3.51-3.41 (m, 1H), 1.49 (s, 6H), 1.20 (d, J=44.2 Hz, 3H), 0.93-0.80 (m, 1H); MS (EI) m/z 629 (MH+).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. customSolvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography (CH2Cl2/MeOH=20:1)

출처 및 근거

ORD 기록
ord-5b8efb379d8b48a29e8ac069d237cf8c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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