Triethylamine → 4-[(3-Oxo-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide

HRID 225502

Reaction equation

HRID 225502 reaction equation
[CH3:1]CCP(=O)=O.C[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)=[CH:10][C:9]=1[NH2:27].[O:28]=[C:29]1[NH:34][CH2:33][CH2:32][N:31]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=2)[CH2:30]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:28]=[C:29]1[NH:34][CH2:33][CH2:32][N:31]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40]([NH:27][C:9]3[CH:8]=[CH:13][C:12]([CH3:1])=[C:11]([NH:14][C:15]4[N:20]=[C:19]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)[CH:18]=[CH:17][N:16]=4)[CH:10]=3)=[O:41])=[CH:38][CH:37]=2)[CH2:30]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 16167369Propylphosphoric anhydrideHCID 167770994-((3-Oxopiperazin-1-yl)methyl)benzoic acidHCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

Product 1

HCID 102176964-[(3-Oxo-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of propylphosphonic anhydride in N,N-dimethylformamide (Fluka, Buchs, Switzerland; 1.3 mL of 50%, 2.25 mmol) is added dropwise to a stirred mixture of 4-methyl-N-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine (416 mg, 1.5 mmol), 4-[(3-oxo-1-piperazinyl)methyl]benzoic acid (351 mg, 1.5 mmol) and triethylamine (1.7 mL, 12 mmol) in dry N,N-dimethylformamide (4 mL). The mixture is stirred for 17 hours at room temperature and then treated with saturated aqueous sodium hydrogen carbonate solution (100 mL). The resulting precipitate is filtered, washed with water, dried and recrystallised from methanol to give the title compound as a cream crystalline solid.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with water
  3. customdried
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-c3e61f6688dc4d85bd0d7f3e4111673b
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Linked notes

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