4-Piperidinecarboxamide → HCID 56646022, compound

HRID 1852412Notes

Reaction equation

HRID 1852412 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[N:21][CH:22]=3)[N:11]=2)[CH:6]=[CH:7][C:8]=1F)#[N:2].[NH:27]1[CH2:32][CH2:31][CH:30]([C:33]([NH2:35])=[O:34])[CH2:29][CH2:28]1>C(O)CCC>[C:24]([NH:23][C:20]1[N:21]=[CH:22][C:17]([NH:16][C:12]2[N:11]=[C:10]([C:5]3[CH:6]=[CH:7][C:8]([N:27]4[CH2:32][CH2:31][CH:30]([C:33]([NH2:35])=[O:34])[CH2:29][CH2:28]4)=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:15]=[CH:14][N:13]=2)=[CH:18][CH:19]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 37724-PiperidinecarboxamideHCID 66685849HCID 66685849, compound

Product 1

HCID 56646022HCID 56646022, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred solution of N-{5-[4-(3-Cyano-4-fluoro-phenyl)-pyrimidin-2-ylamino]-pyridin-2-yl}-acetamide (100 mg, 0.28 mmol) and piperidine-4-carboxylic acid amide in n-butanol (5 mL) was heated to 115° C. in a sealed tube for 48 h. The solvent was evaporated to obtain the crude compound. The crude compound was purified by preparative-HPLC to obtain the desired product as pale yellow powder (38 mg, 29%); LC-MS, Rt,=2.96 min (Method C), m/z 457 (MH+). In addition to this procedure similar reactions may also be accomplished at 110° for 16-120 h. Purification may be by preparative-HPLC or flash column chromatography.

Workup

  1. customThe solvent was evaporated
  2. customto obtain the crude compound
  3. customThe crude compound was purified by preparative-HPLC

Sources & evidence

ORD record
ord-ba36f6cf51c84192997ce073b2ece83d
Source dataset
uspto-grants-2015_02
Patent number
US08962609B2

Reaction notes

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