Hydrochloric Acid → 2-Bromo-5-[(4-chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410113ノート

反応式

HRID 2410113 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)O)=[O:5])[CH3:2].[NH2:24][CH:25]1[CH2:30][N:29]([CH3:31])[C:28](=[O:32])[CH2:27][CH2:26]1.Cl>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[NH:24][CH:25]1[CH2:26][CH2:27][C:28](=[O:32])[N:29]([CH3:31])[CH2:30]1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 510721765-Amino-1-methylpiperidin-2-oneHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate2 回

生成物 1

HCID 867077672-Bromo-5-[(4-chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

The title compound was prepared in analogy to the procedure described for step E2 using 2-bromo-5-[(4-chlorophenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (intermediate B) and 5-amino-1-methylpiperidin-2-one (ChemBridge, free base was made from the purchased HCl salt) as starting materials. The crude reaction mixture was diluted with EtOAc and washed with aqueous NaHCO3 solution and brine. tr: 1.07 min (LC-MS 2); ESI-MS: 511.1 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.42 (m, 2H), 7.30 (m, 2H), 6.28 (NH, br, 1H), 4.85-5.00 (m, 1 H), 4.25 (quin, 2 H), 3.15-3.05 (m, 2H), 2.84-2.75 (m, 1H), 2.72 (d, 3H), 2.38-1.85 (m, 4H), 1.75-1.58 (m, 1), 1.45 (d, 3 H), 1.24 (t, 3 H), 0.83 (t, 3H).

後処理

  1. customThe crude reaction mixture
  2. washwashed with aqueous NaHCO3 solution and brine
  3. custom1.07 min (LC-MS 2)

出典と根拠

ORDレコード
ord-f64b30b3576f498ea11f35cef7a3b6f6
出典データセット
uspto-grants-2014_08
特許番号
US08815926B2

反応ノート

読み込み中…