4-Methoxybenzylamine → HCID 89906624、化合物

HRID 525742ノート

反応式

HRID 525742 の反応式
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([C:13]([NH:15][CH2:16][C:17]#[CH:18])=O)=[CH:11][C:10]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[O:20])=[CH:9][N:8]=2)[CH2:3]1.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Zn+2].FC(F)(F)S([O-])(=O)=O>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([C:13]3[N:40]([CH2:39][C:38]4[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=4)[C:17]([CH3:18])=[CH:16][N:15]=3)=[CH:11][C:10]([C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:30])[F:32])=[CH:26][CH:27]=3)=[O:20])=[CH:9][N:8]=2)[CH2:3]1

参加物

5

反応物 2

HCID 754524-MethoxybenzylamineHCID 89907813HCID 89907813、化合物

生成物 1

HCID 89906624HCID 89906624、化合物

試薬・触媒・溶媒 2

HCID 104671Zinc trifluoromethanesulfonate触媒HCID 1140Toluene溶媒

実験手順

A stirred mixture of (R)-2-(3-hydroxypyrrolidin-1-yl)-N3-(prop-2-yn-1-yl)-N5-(4-(trifluoromethoxy)phenyl)pyridine-3,5-dicarboxamide (Stage 72.2, 0.50 g, 1.115 mmol) and 4-methoxybenzylamine (0.175 mL, 1.338 mmol) in toluene (30 mL) was treated with zinc trifluoromethanesulphonate (61 mg, 0.17 mmol) and heated under reflux for 41 h. The solvent was evaporated off under reduced pressure and the crude product was purified by flash chromatography (RediSep® Silica gel column, EtOAc 100%) to afford the title compound as a foam. HPLC (Condition 4) tR=4.66 min, UPLC-MS (Condition 8) tR=0.93 min, m/z=568.1 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.72 (br. s, 1H), 2.19 (s, 3H), 2.74-3.09 (m, 2H), 2.85-3.07 (m, 1H), 3.15-3.31 (m, 2H), 3.64 (s, 3H), 4.15 (br. s, 1H), 4.90 (m, 3H), 6.72-6.86 (m, 5H), 7.35 (d, J=8.59 Hz, 2H), 7.85 (d, J=8.42 Hz, 2H), 7.19-8.03 (m, 1H), 8.78 (br. s, 1H), 10.05-10.20 (m, 1H).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 41 h
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe crude product was purified by flash chromatography (RediSep® Silica gel column, EtOAc 100%)

出典と根拠

ORDレコード
ord-e293d7b1799c499ea7c65035c755634e
出典データセット
uspto-grants-2016_05
特許番号
US09340537B2

反応ノート

読み込み中…