1,2-Dichloroethane → Methyl cis-2-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylate

HRID 1631042ノート

反応式

HRID 1631042 の反応式
[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])=[N:4][CH:5]=[C:6]([C:8](=[N:10][OH:11])[NH2:9])[CH:7]=1.Br[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=O)=[CH:25][C:24]=1[CH2:33]OC.[CH2:36](Cl)[CH2:37]Cl>CC#N.N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[C:18]([O:20][CH3:21])=[O:19])=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[C:33]([C:24]3[CH:23]=[CH:32][C:31]([C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][C:36]=4[CH3:37])=[C:26]([CH2:27][O:29][CH3:30])[CH:25]=3)[O:11][N:10]=2)[CH:7]=1

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 90293497cis-Methyl 2-(3-chloro-5-(n'-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylate

生成物 1

HCID 67135658Methyl cis-2-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-ylamino)cyclopentanecarboxylate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of cis-methyl 2-(3-chloro-5-(N′-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylate (0.172 g; 0.55 mmol) and Intermediate A1 (0.155 g; 0.60 mmol) in MeCN (2 mL) was added EDC (0.117 g; 0.61 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (2 mL) and heated at 150° C. in the microwave for 30 minutes. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (4:1) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.84 (1H, d, J=2 Hz), 8.40 (1H, s), 8.21 (1H, d, J=2), 8.15-8.10 (1H, m), 7.34-7.26 (4H, m), 7.13 (1H, d, J=7.5 Hz), 5.91 (1H, d, J=8.3 Hz), 4.83 (1H, m), 4.22-4.13 (2H, m), 3.63 (3H, s), 3.33 (3H, s), 3.23-3.17 (1H, m), 2.21-1.63 (9H, m).

後処理

  1. temperatureheated at 150° C. in the microwave for 30 minutes
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washThe mixture was washed with water
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica
  7. washeluting with iso-hexane/EtOAc (4:1)

出典と根拠

ORDレコード
ord-fa2f0079e3c54211b6341510b726c5fa
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

読み込み中…