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

HRID 20632Notes

Reaction equation

HRID 20632 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-49d570f5b6da402d8ae3be1663819276
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

Loading…