Trifluoroacetic anhydride → 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-hydroxy-7-methoxy-2H-chromen-2-one

HRID 20632

反応式

HRID 20632 の反応式
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH:14]1([O:19][C:20]2[C:21]([O:40][CH3:41])=[CH:22][CH:23]=[C:24]3[C:29]=2[O:28][C:27](=[O:30])[CH:26]=[C:25]3[NH:31][C:32]2[C:37]([Cl:38])=[CH:36][N:35]=[CH:34][C:33]=2[Cl:39])[CH2:18][CH2:17][CH2:16][CH2:15]1.NC(N)=O.OO.[O-]S([O-])(=S)=O.[Na+].[Na+]>Cl.ClCCl>[CH:14]1([O:19][C:20]2[C:21]([O:40][CH3:41])=[CH:22][CH:23]=[C:24]3[C:29]=2[O:28][C:27](=[O:30])[C:26]([OH:4])=[C:25]3[NH:31][C:32]2[C:37]([Cl:38])=[CH:36][N:35]=[CH:34][C:33]=2[Cl:39])[CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

7

反応物 4

HCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 31294Carbamide PeroxideHCID 248493808-(cyclopentyloxy)-4-[(3,5-dichloropyridin-4-yl)amino]-7-methoxy-2H-chromen-2-one

生成物 1

HCID 248493818-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-hydroxy-7-methoxy-2H-chromen-2-one

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic anhydride (0.04 mL, 0.29 mmol) was added to a solution of 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (42 mg, 0.1 mmol, Example 3), urea•H2O2 (28.5 mg, 0.3 mmol), and dichloromethane (2 mL) at rt under N2. After 1.5 h, sat'd Na2S2O3 (8 mL) was added, and the mixture was stirred vigorously for 15 min. The reaction was then diluted with 0.5N HCl (40 mL), and extracted with dichloromethane (40 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (4:1→1:1; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-3-hydroxy-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 8.42 (s, 2H), 8.40 (s, 1H), 7.59 (d, 1H), 7.12 (d, 1H), 4.84 (m, 1H), 3.86 (s, 3H), 1.90-1.50 (m, 8H); MS (ESI): 436.9.

後処理

  1. extractionextracted with dichloromethane (40 mL×2)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (4:1→1:1; hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-49d570f5b6da402d8ae3be1663819276
出典データセット
uspto-grants-2010_06
特許番号
US07745646B2

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