Sodium hydride → 8-(cyclopentyloxy)-4-[(3,5-dichloropyridin-4-yl)amino]-7-methoxy-2H-chromen-2-one

HRID 20631Notes

Reaction equation

HRID 20631 reaction equation
[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.[Cl:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Cl:31])[C:29]=1Cl.OP([O-])(O)=O.[K+]>CS(C)=O>[CH:17]1([O:16][C:9]2[C:10]([O:14][CH3:15])=[CH:11][CH:12]=[C:13]3[C:8]=2[O:7][C:6](=[O:22])[CH:5]=[C:4]3[NH:3][C:29]2[C:28]([Cl:31])=[CH:27][N:26]=[CH:25][C:24]=2[Cl:23])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516951Monobasic potassium phosphateHCID 37865313,4,5-TrichloropyridineHCID 771747934-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248493808-(cyclopentyloxy)-4-[(3,5-dichloropyridin-4-yl)amino]-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (12 mg, 60%, 0.30 mmol) was added to a solution of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (40 mg, 0.15 mmol), 3,4,5-trichloropyridine (27 mg, 0.15 mmol), and anhydrous DMSO (3 mL) at rt under N2. After 4 h, the reaction was poured into 1M KH2PO4 (40 mL) and extracted with ethyl acetate (40 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (13:7→9:11; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.50 (s, 1H), 8.81 (s, 2H), 7.93 (d, 1H), 7.20 (d, 1H), 4.83 (m, 1H), 4.63 (s, 1H), 3.91 (s, 3H), 1.80-1.00 (m, 8H); MS (ESI): 421.1.

Workup

  1. extractionextracted with ethyl acetate (40 mL×2)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (13:7→9:11; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-d4303892e9524db4b85c7ed3e94a1a77
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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