Dimethylamine → Methyl 2-[(dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylate

HRID 400746ノート

反応式

HRID 400746 の反応式
C(O[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])(=O)C.C[CH2:24][N:25](C(C)C)[CH:26](C)C.CS(Cl)(=O)=O.CNC>C(Cl)Cl>[CH3:24][N:25]([CH2:5][C:6]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])[CH3:26]

参加物

6

反応物 4

HCID 674DimethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67400282Methyl 2-[(acetyloxy)methyl]-2'-methylbiphenyl-4-carboxylate

生成物 1

HCID 66678469Methyl 2-[(dimethylamino)methyl]-2'-methylbiphenyl-4-carboxylate収率 86.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 2-(hydroxymethyl)-2′-methylbiphenyl-4-carboxylate obtained in step 3 (2.12 g; 8.27 mmol) in DCM (63.6 mL) was added at 0° C. DIEA (7.03 mL; 41.36 mmol) and methanesulfonyl chloride (768 μL; 9.93 mmol) at 0° C. and stirred at 25 min. After this time, dimethylamine (12.41 mL; 2 M; 24.81 mmol) was added to the reaction mixture and stirred at RT for 16 hours. Reaction mixture was partitioned between DCM and an aqueous solution of NaOH (5 M). Purification by silica column chromatography (DCM/[DCM/MeOH 2:1] gradient) gave the title compound as a light yellow solid (2.03 g, 86%). 1H NMR (DMSO-d6) δ 8.27 (d, J=1.4 Hz, 1H), 7.95 (dd, J=7.8, 1.9 Hz, 1H), 7.32-7.18 (m, 4H), 7.06 (d, J=7.3 Hz, 1H), 3.94 (s, 3H), 3.24-3.10 (m, 2H), 2.11 (s, 6H), 2.01 (s, 3H). HPLC (Method A) Rt 2.90 min (Purity 100.0%). LC/MS (Method B): 284.1 (M−H)−.

後処理

  1. customReaction mixture
  2. customwas partitioned between DCM
  3. customPurification by silica column chromatography (DCM/[DCM/MeOH 2:1] gradient)

出典と根拠

ORDレコード
ord-a13e410aad704692a71375e5e8e4f026
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

反応ノート

読み込み中…