Sodium hydride → 4-[4-(tert-Butoxycarbonyl)-2-methylpiperazin-1-yl]-7-chloroquinoline

HRID 1353353Notes

Reaction equation

HRID 1353353 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[CH2:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH:24]([CH3:28])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:8]2[C:7]3[C:12](=[CH:13][C:4]([Cl:3])=[CH:5][CH:6]=3)[N:11]=[CH:10][CH:9]=2)[CH:24]([CH3:28])[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylateHCID 69514546HCID 69514546, compound

Product 1

HCID 211017004-[4-(tert-Butoxycarbonyl)-2-methylpiperazin-1-yl]-7-chloroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (72 mg, 3 mmol) is added to a solution of 7-chloro-4-quinolone (359 mg, 2 mmol) in DMF. After 1 h at 40° C. N-phenyl(trifluoromethylsulfon)imide (1.0 g, 2.8 mmol) and, 1 h later, 1-tert-butoxycarbonyl-3-methylpiperazine (1.8 g, 8 mmol) is added. The reaction mixture is stirred at 80° C. for 2 days, concentrated, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and concentrated. The residue is purified by reversed phase HPLC with water-MeCN-TFA to give the title product.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by reversed phase HPLC with water-MeCN-TFA

Sources & evidence

ORD record
ord-30f3e73dbdeb44cbbcc5934bf9abe4e9
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…