Dimethyl Sulfoxide → 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20640ノート

反応式

HRID 20640 の反応式
[H-].[Na+].[NH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[O:7][C:6](=[O:22])[CH:5]=1.CS(C)=O.[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:35])[C:33]=1Cl>[Cl-].[Na+].O>[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:35])[C:33]=1[NH:3][C:4]1[C:13]2[C:8](=[C:9]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[O:7][C:6](=[O:22])[CH:5]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 687426533-Bromo-4,5-dichloropyridineHCID 771747934-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

生成物 1

HCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

Sodium hydride (7 mg, 60%, 0.18 mmol) was added to a solution of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (77 mg, 0.28 mmol, Example 3, Step 1) and anhydrous DMSO (3 mL) under N2. After 10 min, 3-bromo-4,5-dichloropyridine (69 mg, 0.31 mmol) was added, and the reaction was stirred for 20 h, poured into brine, and extracted with EtOAc. The organic extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (20→100% MeCN/H2O) to give 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.54 (s, 1H), 8.91 (s, 1H), 8.84 (s, 1H), 7.95 (d, 1H), 7.21 (d, 1H), 4.85 (m, 1H), 4.59 (s, 1H), 3.92 (s, 3H), 1.87-1.79 (m, 4H), 1.68-1.54 (m, 4H); MS (ESI): 464.7.

後処理

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. customwas dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse-phase HPLC (20→100% MeCN/H2O)

出典と根拠

ORDレコード
ord-dccd032796f642beb0e66a4b9d608b32
出典データセット
uspto-grants-2010_06
特許番号
US07745646B2

反応ノート

読み込み中…