4-Piperidinecarboxamide → HCID 59333598, compound

HRID 1876543Notes

Reaction equation

HRID 1876543 reaction equation
CN1CCCC1=O.Cl[C:9]1[N:10]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:11]2[C:16]([N:17]=1)=[C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:14]=[C:13]([C:24]1[C:25]([CH3:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=1)[N:12]=2.[NH:36]1[CH2:44][CH2:43][CH:39]([C:40]([NH2:42])=[O:41])[CH2:38][CH2:37]1>O>[NH2:30][C:27]1[N:26]=[C:25]([CH3:31])[C:24]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:9]([N:36]4[CH2:44][CH2:43][CH:39]([C:40]([NH2:42])=[O:41])[CH2:38][CH2:37]4)[N:10]3[CH2:32][CH:33]3[CH2:35][CH2:34]3)=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:14]=2)=[CH:29][N:28]=1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 13387N-methyl-2-pyrrolidoneHCID 59333498HCID 59333498, compound

Product 1

HCID 59333598HCID 59333598, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

N-Methylpyrrolidone (1 ml) was added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.25 mmol) and isonipecotamide (191 mg, 1.5 mmol) and the resulting mixture was stirred at 120° C. for 2.5 hours. The reaction mixture was left standing to cool followed by the addition of water and the insoluble matter was collected by filtration and dried to give 1-[2-(2-amino-4-methylpyrimidin-5-yl)-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-8-yl]piperidine-4-carboxamide (85 mg, 69%) as a pale yellow solid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. filtrationthe insoluble matter was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-55d47e2588fd4f80877a517896d7df3a
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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