1-Methylpiperazine → HCID 53346254, compound

HRID 1095795Notes

Reaction equation

HRID 1095795 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][O:12][C:13]1[C:14]([O:33][CH3:34])=[CH:15][CH:16]=[C:17]2[C:22]=1[NH:21][C:20](=[O:23])[CH:19]=[C:18]2[NH:24][C:25]1[C:30]([Cl:31])=[CH:29][N:28]=[CH:27][C:26]=1[Cl:32]>CS(C)=O>[Cl:32][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:31])[C:25]=1[NH:24][C:18]1[C:17]2[C:22](=[C:13]([O:12][CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:14]([O:33][CH3:34])=[CH:15][CH:16]=2)[NH:21][C:20](=[O:23])[CH:19]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 66780790HCID 66780790, compound

Product 1

HCID 53346254HCID 53346254, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Methylpiperazine (0.5 mL, 4.5 mmol) was added to a solution of 8-(3-bromopropoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (150 mg, 0.32 mmol) and DMSO (2 mL) at room temperature. After 15 h, the reaction was placed under vacuum (˜0.1 Torr, 24h) to remove the excess amine. The resulting solution was purified by reverse-phase HPLC to give 4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-8-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-2(1H)-one. 1H NMR (400 MHz, DMSO-d6, bis HCl salt): δ 12.01 (br, 2H), 10.80 (br, 1H), 9.21 (s, 1H), 8.79 (s, 2H), 8.01 (d, 1H), 7.15 (d, 1H), 4.94 (s, 1H), 4.04 (t, 2H), 3.95 (s, 3H), 3.90-3.60 (br m, 4H), 3.60-3.34 (br m, 6H), 2.82 (s, 3H), 2.25 (m, 2H); MS (ESI): 492.3.

Workup

  1. customto remove the excess amine
  2. customThe resulting solution was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-314ba49acba447e4bb85950884b0eeba
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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