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

HRID 20674

Reaction equation

HRID 20674 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([O:35][CH3:36])=[CH:17][CH:18]=[C:19]2[C:24]=1[O:23][C:22](=[O:25])[CH:21]=[C:20]2[NH:26][C:27]1[C:32]([Cl:33])=[CH:31][N:30]=[CH:29][C:28]=1[Cl:34].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:34][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:33])[C:27]=1[NH:26][C:20]1[C:19]2[C:24](=[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:16]([O:35][CH3:36])=[CH:17][CH:18]=2)[O:23][C:22](=[O:25])[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 248495698-(5-Bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248497584-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-(5-(4-methylpiperazin-1-yl)pentyloxy)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Methylpiperazine (0.2 mL, 1.8 mmol) was added to a solution of 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (50 mg, 0.1 mmol, Example 28) and DMSO (1.5 mL). After 10 h, the reaction was poured into 10% K2CO3 (30 mL) and extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried, filtered, concentrated, and purified by reverse-phase HPLC (acetonitrile:water) to give 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-(5-(4-methylpiperazin-1-yl)pentyloxy)-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.45 (br s, 1H), 8.71 (s, 2H), 7.90 (d, 1H), 7.13 (d, 1H), 4.46 (br s, 1H), 3.97 (t, 2H), 3.90 (s, 3H), 2.60-2.20 (br, 10H), 2.21 (s, 3H), 1.68 (m, 2H), 1.47 (m, 4H); MS (ESI): 520.9.

Workup

  1. extractionextracted with ethyl acetate (30 mL×3)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (acetonitrile:water)

Sources & evidence

ORD record
ord-282594710d444ce4b747398bd6f38e23
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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