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

HRID 20632

반응식

HRID 20632 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-49d570f5b6da402d8ae3be1663819276
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745646B2

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