Dimethylformamide → HCID 117840115, compound

HRID 1477570Notes

Reaction equation

HRID 1477570 reaction equation
CN(C)C=O.[O:6]=[C:7]1[NH:12][CH:11]=[N:10][C:9]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:8]1.C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1>O>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:12]2[CH:11]=[N:10][C:9]([N:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[N:8][C:7]2=[O:6])=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 178452267HCID 178452267, compound

Product 1

HCID 117840115HCID 117840115, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide solution (200 mL) of the crude product of tert-butyl 4-(4-oxo-4,5-dihydro-1,3,5-triazin-2-yl)piperazine-1-carboxylate synthesized in Reference Synthesis Example 7 and potassium carbonate (7.46 g, 54.0 mmol), 4-chlorobenzyl bromide (10.2 g, 49.5 mmol) was added at room temperature and the resultant reaction solution was stirred at room temperature for 1 day. After completion of the reaction, water was added to the reaction solution and a deposited solid was collected by filtration. The filtered residue was suspended in ethyl acetate and the suspended solid was collected by filtration and dried under reduced pressure to obtain the title compound (12.4 g, two step yield 68%).

Workup

  1. additionwas added at room temperature
  2. customthe resultant reaction solution
  3. additionwas added to the reaction solution
  4. filtrationa deposited solid was collected by filtration
  5. filtrationthe suspended solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-20087a7b39d14e9ca2f312a624d06d5e
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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