Dimethylformamide → Tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate

HRID 454653Notes

Reaction equation

HRID 454653 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1.[CH2:23]([O:30][C:31]1[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][C:32]=1[C:33]([NH:35][C:36]1[CH:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:46]=[CH:45][C:37]=1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.O>[CH2:23]([O:30][C:31]1[CH:58]=[CH:57][C:56]([O:59][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:55][C:32]=1[C:33]([NH:35][C:36]1[CH:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:46]=[CH:45][C:37]=1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 414088HCID 414088, compoundHCID 66990772Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate

Product 1

HCID 66990152Tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoateYield 31.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

N,N-Dimethylformamide (3.0 mL), potassium carbonate (0.12 g), and 1-(3-bromopropyl)-4-methylpiperazine (0.30 g) were sequentially added to tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate (0.15 g), followed by stirring at 100° C. for 1 hour and 20 minutes. Potassium carbonate (0.12 g) was added to the reaction mixture, followed by stirring at 100° C. for 50 minutes. Water and chloroform were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol] to obtain 0.060 g of tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate.

Workup

  1. stirringby stirring at 100° C. for 50 minutes
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Sources & evidence

ORD record
ord-4c15c95ecc96431c95e83a990959c2e0
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…