Water → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-5-piperidin-1-yl-benzamide

HRID 1687149Notes

Reaction equation

HRID 1687149 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.O>C1COCC1>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:7][C:3]=2[C:4]([NH2:6])=[O:5])[C:27]([Cl:31])=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 107276062-Amino-5-(piperidin-1-yl)benzamide

Product 1

HCID 866338852-(2,5-Dichloro-pyrimidin-4-ylamino)-5-piperidin-1-yl-benzamideYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-piperidin-1-yl-benzamide (1.05 g, 4.6 mmol, Heterocyclic Comm. 2001, 7, 473-480) in THF (10 mL) was added K2CO3 (0.76 g, 5.5 mmol) and 2,4,5-trichloropyrimidine (0.84 g, 4.6 mmol). After stirring for 72 h, addition of water (5 mL) gave a precipitate that was removed by filtration and washed with water (5×3 mL) and ether (3×2 mL) to afford 2-(2,5-dichloro-pyrimidin-4-ylamino)-5-piperidin-1-yl-benzamide as a yellow solid (0.99 g) that was used without further purification in the subsequent step.

Workup

  1. customgave a precipitate that
  2. customwas removed by filtration
  3. washwashed with water (5×3 mL) and ether (3×2 mL)

Sources & evidence

ORD record
ord-a5b68180a5ed492bb5df58e9a3c2f4f6
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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