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Pyridine → 2-(2-(2-(2-((1-(1-Acetylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592468
Notes
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Reaction equation

HRID 592468 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH:34]([CH3:38])[C:35]([NH2:37])=[O:36])[C:23]([C:39]([F:42])([F:41])[F:40])=[CH:22][N:21]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH:34]([CH3:38])[C:35]([NH2:37])=[O:36])[C:23]([C:39]([F:41])([F:40])[F:42])=[CH:22][N:21]=3)[CH:16]=[N:15]2)[CH2:12][CH2:13]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 732951232-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-ylethyl)phenyl)propanamide

Product 1

HCID 732952932-(2-(2-(2-((1-(1-Acetylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Acetic anhydride (15 μL, 0.15 mmol) was added to a solution of 2-(2-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide 56 (50 mg, 0.10 mmol) in DCM (5 mL) and pyridine (12 μL, 0.15 mmol) and the mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the resultant solid was suspended in water (25 mL) and sonicated for 5 minutes. The solid was collected by filtration and washed with sat. aq. Na2CO3 (20 mL), water (50 mL) then petroleum benzine 40-60° C. to give the title compound 58 as a white solid (42 mg, 77%). LCMS-D: rt 3.176 min; m/z 530.4 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customsonicated for 5 minutes
  3. filtrationThe solid was collected by filtration
  4. washwashed with sat. aq. Na2CO3 (20 mL), water (50 mL)

Sources & evidence

ORD record
ord-0b4f120617594a7a9cdf21d47126eaf2
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238644B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes