Dimethylformamide → HCID 11697660, compound

HRID 2167067Notes

Reaction equation

HRID 2167067 reaction equation
ClC1C=C2C(C(N[CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][NH:25][C:26]4[C:35]5[C:30](=[CH:31][C:32]([Cl:36])=[CH:33][CH:34]=5)[N:29]=[CH:28][CH:27]=4)[CH2:18][CH2:17]3)=CC=N2)=CC=1.Br[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Br.C([O-])([O-])=O.[K+].[K+].C[N:51](C=O)C>>[Cl:36][C:32]1[CH:31]=[C:30]2[C:35]([C:26]([NH:25][CH2:24][CH2:23][CH2:22][N:19]3[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][N:51]4[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]4)[CH2:21][CH2:20]3)=[CH:27][CH:28]=[N:29]2)=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 11670888HCID 11670888, compound

Product 1

HCID 11697660HCID 11697660, compound

Procedure

To a solution of 1,4-bis{3-[N-(7-chloroquinolin-4-yl)amino]propyl}piperazine described in example 1 (0.15 g, 0.41 mmol), 1,5-dibromopentane (0.068 mL, 0.5 mmol) in DMF (5 mL), K2CO3 (287 mg, 2.07 mmol) is added. After stirring the mixture at room temperature for 48 h, the solvent was removed under reduced pressure. The residue was solubilized in CH2Cl2, washed with NaHCO3 1M and dried over MgSO4. Crude compound is purified by thick-layer chromatography (CH2Cl2/MeOH/NH4OH: 80/20/2.7).

Workup

  1. additionis added
  2. customthe solvent was removed under reduced pressure
  3. washwashed with NaHCO3 1M
  4. dry with materialdried over MgSO4
  5. customCrude compound is purified by thick-layer chromatography (CH2Cl2/MeOH/NH4OH: 80/20/2.7)

Sources & evidence

ORD record
ord-da0746970b0a4a5e88616315f3bbabca
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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