Dimethylamine → HCID 53346253, compound

HRID 1095793Notes

Reaction equation

HRID 1095793 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][CH:12]=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[C:14]2[NH:20][C:21]1[C:26]([Cl:27])=[CH:25][N:24]=[CH:23][C:22]=1[Cl:28].[CH3:31][NH:32][CH3:33]>CS(C)=O>[Cl:28][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([Cl:27])[C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]([CH3:33])[CH3:31])[C:10]([O:29][CH3:30])=[CH:11][CH:12]=2)[NH:17][C:16](=[O:19])[CH:15]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 66781767HCID 66781767, compound

Product 1

HCID 53346253HCID 53346253, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

8-(6-Bromohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (129 mg, 0.25 mmol) was added to a solution of dimethylamine (2.0 mL, 2M tetrahydrofuran, 4 mmol) and DMSO (0.5 mL) at room temperature. After 2.5 h, the reaction was concentrated to remove the excess amine and tetrahydrofuran. The resulting solution was purified by reverse-phase HPLC to give 4-(3,5-dichloropyridin-4-ylamino)-8-(6-(dimethylamino)hexyloxy)-7-methoxyquinolin-2(1H)-one. 1H NMR (400 MHz, DMSO-d6, HCl salt): δ 10.32 (s, 1H), 10.27 (br, 1H), 9.14 (s, 1H), 8.78 (s, 2H), 7.97 (d, 1H), 7.12 (d, 1H), 4.90 (s, 1H), 3.99 (t, 2H), 3.92 (s, 3H), 2.99 (m, 2H), 2.70 (d, 6H), 1.77 (m, 2H), 1.65 (m, 2H), 1.43 (m, 2H), 1.33 (m, 2H); MS(ESI): 479.0.

Workup

  1. concentrationthe reaction was concentrated
  2. customto remove the excess amine and tetrahydrofuran
  3. customThe resulting solution was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-e9958a2173904fbeb0df2cc801e9708f
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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