Potassium Carbonate → 8-(5-(1H-1,2,3-triazol-1-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

HRID 20715Notes

Reaction equation

HRID 20715 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21](=[O:24])[CH:20]=[C:19]2[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33].[NH:36]1[CH:40]=[CH:39][N:38]=[N:37]1>CN(C=O)C>[N:36]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21](=[O:24])[CH:20]=[C:19]3[NH:25][C:26]2[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=2[Cl:33])[CH:40]=[CH:39][N:38]=[N:37]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 248495698-(5-Bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-oneHCID 178418936HCID 178418936, compound

Product 1

HCID 248493858-(5-(1H-1,2,3-triazol-1-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (350 mg, 2.54 mmol) was added to a solution of 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (1.0 g, 2.0 mmol, Example 28), 1H-1,2,3-triazole (210 mg, 3.04 mmol), and DMF (15 mL) at rt. After 3.5 h at 80° C., the mixture was allowed to cool to rt, quenched with water (10 mL), and then extracted with ethyl acetate (20 mL×3). The combined extracts were washed with brine, dried, filtered, concentrated, and then purified by silica gel chromatography (dichloromethane:methanol) to give 8-(5-(1H-1,2,3-triazol-1-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 8.81 (s, 2H), 8.13 (s, 1H), 7.94 (d, 1H), 7.69 (s, 1H), 7.19 (d, 1H), 4.63 (s, 1H), 4.40 (t, 2H), 3.97 (t, 2H), 3.90 (s, 3H), 1.88 (m, 2H), 1.75 (m, 2H), 1.45 (m, 2H); MS (ESI): 490.0.

Workup

  1. customquenched with water (10 mL)
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. washThe combined extracts were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (dichloromethane:methanol)

Sources & evidence

ORD record
ord-10f87438b6454f3aa40f05ecc84f22af
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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