Triethylamine → HCID 10480859, compound

HRID 2099438Notes

Reaction equation

HRID 2099438 reaction equation
CCCP(=O)=O.[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[NH:17][C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)[CH2:33][CH2:32]1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O>[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:44][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][N:34]3[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]3)=[CH:43][CH:42]=2)=[O:14])=[CH:10][C:9]=1[NH:17][C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 104028804-Methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acidHCID 16167369Propylphosphoric anhydride

Product 1

HCID 10480859HCID 10480859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution containing ˜50% of propylphosphonic anhydride in N,N-dimethylformamide (Fluka, Buchs, Switzerland; 875 μL, ˜1.5 mmol) is added within 20 minutes to a stirred mixture of 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzoic acid (306 mg, 1.0 mmol), 4-[(4-methyl-1-piperazinyl)methyl]benzeneamine (Chem. Abstr. Reg. Number: 70261-82-4; 205 mg, 1.0 mmol) and triethylamine (830 μL, 6.0 mmol) in 8 mL N,N-dimethylformamide. After stirring for 24 hours at room temperature, the mixture is treated with a saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The solvent is evaporated off under reduced pressure and the residue dried in vacuo. The crude product is crystallised from ethanol-ethyl acetate to give the title compound as a crystalline solid, m.p. 153-155° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customThe solvent is evaporated off under reduced pressure
  3. customthe residue dried in vacuo
  4. customThe crude product is crystallised from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-b36b4960f7c14c0f921f6873df9b1fe3
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

Loading…