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

HRID 400746노트

반응식

HRID 400746 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)−.

후처리

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

출처 및 근거

ORD 기록
ord-a13e410aad704692a71375e5e8e4f026
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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