Water → HCID 58513105, compound

HRID 1405054Notes

Reaction equation

HRID 1405054 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=1.[CH2:19]([O:21][C:22]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[CH3:20].O>CN1C(=O)CCC1>[CH2:19]([O:21][C:22]([CH:24]1[CH2:29][CH2:28][N:27]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[C:6]([CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=2)[CH2:26][CH2:25]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 70770Ethyl 4-piperidinecarboxylateHCID 58513427HCID 58513427, compound

Product 1

HCID 58513105HCID 58513105, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound is synthesized according to general procedure GP7 starting from 2.0 g (7.7 mmol) 4-chloro-6-methyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidin-2-ylamine and 1.33 g (8.47 mmol) piperidine-4-carboxylic acid ethyl ester using 1.18 mL (8.5 mmol) triethylamine in 12 mL NMP. Work up is performed by addition of 50 mL water to the reaction mixture and stirring for 30 min. The solid material is filtered off, washed with water (50 mL three times) yielding 1.58 g (4.15 mmol) of the desired product with sufficient purity.

Workup

  1. customThe title compound is synthesized
  2. filtrationThe solid material is filtered off
  3. washwashed with water (50 mL three times)

Sources & evidence

ORD record
ord-2a77f7c812084c7da84dbce9ff3ef017
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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