Pyridine → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-4'-methanesulfonylamino-biphenyl-4-yl)-amide

HRID 1711250노트

반응식

HRID 1711250 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[C:10]([C:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]=3)[CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[C:32]1([C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:45]([CH3:44])(=[O:47])=[O:46])=[CH:7][CH:6]=3)[CH:13]=[CH:12][C:11]=2[NH:14][C:15]([C:17]2[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:31])[CH3:29])[CH:19]=[C:20]([C:22]#[N:23])[N:21]=2)=[O:16])[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 587548184-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4'-amino-3-cyclohex-1-enyl-biphenyl-4-yl)-amide

생성물 1

HCID 587548254-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (3-cyclohex-1-enyl-4'-methanesulfonylamino-biphenyl-4-yl)-amide수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4′-amino-3-cyclohex-1-enyl-biphenyl-4-yl)-amide (as prepared in the Example 28, step (a), 28.1 mg, 0.0547 mmol) in 0.5 mL of DCM was added pyridine (113 μL, 0.16 mmol) followed by methanesulfonyl chloride (5.1 μL, 0.066 mmol). After stirring at RT for 16 h under Ar, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (2-4% EtOAc/DCM) to afford 31 mg (95%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 9.79 (s, 1H), 8.42 (d, 1H, J=8.6 Hz), 7.79 (s, 1H), 7.58 (d, 2H, J=8.6 Hz), 7.48 (dd, 1H, J=8.6, 2.3 Hz), 7.37 (s, 1H), 7.29 (d, 2H, J=8.6 Hz), 6.64 (s, 1H), 5.97 (s, 2H), 5.91 (m, 1H), 3.68 (t, 2H, J=8.2 Hz), 3.05 (s, 3H), 2.24-2.38 (m, 4H), 1.75-1.93 (m, 4H), 0.99 (t, 2H, J=8.2 Hz), 0.01 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C30H37N5O4SSi, 592.2 (M+H), found 591.6.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel (2-4% EtOAc/DCM)

출처 및 근거

ORD 기록
ord-77c5a39aca03432aba985744807f1690
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790724B2

반응 노트

불러오는 중…