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

HRID 1711250ノート

反応式

HRID 1711250 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-77c5a39aca03432aba985744807f1690
出典データセット
uspto-grants-2010_09
特許番号
US07790724B2

反応ノート

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