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、化合物

HRID 1627305ノート

反応式

HRID 1627305 の反応式
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]

参加物

4

反応物 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、化合物

生成物 1

HCID 178490000HCID 178490000、化合物収率 57.1%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-5b8efb379d8b48a29e8ac069d237cf8c
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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