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Dicyclohexylcarbodiimide → 4-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamide

HRID 1926592
Notes
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Reaction equation

HRID 1926592 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:33][C:34]1[CH:35]=[C:36]([NH:41][C:42]2[N:47]=[C:46]([C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)[CH:45]=[CH:44][N:43]=2)[C:37]([CH3:40])=[N:38][CH:39]=1>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:33][C:34]3[CH:39]=[N:38][C:37]([CH3:40])=[C:36]([NH:41][C:42]4[N:47]=[C:46]([C:48]5[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=5)[CH:45]=[CH:44][N:43]=4)[CH:35]=3)=[O:15])=[CH:16][CH:17]=2)[CH2:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acidHCID 469098562-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMine

Product 1

HCID 692278004-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a flask was added 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (3.2 g), dicyclohexylcarbodiimide (3.0 g), N-(5-amino-2-methylpyridin-3-yl)-4-(3-pyridyl)pyrimidin-2-amine (3.0 g) and CH2Cl2 (100 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtrated and the filtrate was washed with water (100 mL×2), dried, filtrated, concentrated, and purified through column chromatography to give 4-[(4-methylpiperazin-1-yl)methyl]-N-{6-methyl-5-[(4-(pyrid-3-yl)pyrimid-2-yl)amino]pyrid-3-yl}benzamide (4.0 g).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. washthe filtrate was washed with water (100 mL×2)
  3. customdried
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. custompurified through column chromatography

Sources & evidence

ORD record
ord-0b3883f5078e4a63a80a15da31216315
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183242B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes