Dimethylamine → 4-(3,5-dichloropyridin-4-ylamino)-8-(4-(dimethylamino)butoxy)-7-methoxy-2H-chromen-2-one

HRID 20653Notes

Reaction equation

HRID 20653 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:30][CH3:31])=[CH:12][CH:13]=[C:14]2[C:19]=1[O:18][C:17](=[O:20])[CH:16]=[C:15]2[NH:21][C:22]1[C:27]([Cl:28])=[CH:26][N:25]=[CH:24][C:23]=1[Cl:29]>CS(C)=O>[Cl:29][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([Cl:28])[C:22]=1[NH:21][C:15]1[C:14]2[C:19](=[C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][N:2]([CH3:3])[CH3:1])[C:11]([O:30][CH3:31])=[CH:12][CH:13]=2)[O:18][C:17](=[O:20])[CH:16]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 248495678-(4-bromobutoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 236492924-(3,5-dichloropyridin-4-ylamino)-8-(4-(dimethylamino)butoxy)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of dimethylamine (3 mL, 2M THF, 6 mmol) was added to a solution of 8-(4-bromobutoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (293 mg, 0.6 mmol, Example 25) and DMSO (6 mL). After 1 h, the reaction was concentrated and purified by reverse-phase HPLC (1:4→3:2; acetonitrile:water) to give 4-(3,5-dichloropyridin-4-ylamino)-8-(4-(dimethylamino)butoxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.53 (br s, 1H), 8.58 (s, 2H), 7.87 (d, 1H), 7.07 (d, 1H), 4.22 (br s, 1H), 3.99 (t, 2H), 3.90 (s, 3H), 2.76 (br, 2H), 2.47 (s, 6H), 1.85-1.65 (m, 4H); MS (ESI): 451.9.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by reverse-phase HPLC (1:4→3:2; acetonitrile:water)

Sources & evidence

ORD record
ord-042caa70a2374a4bb767f5a4a9d06893
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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