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Aniline → (3S,6R)-1-[6-Chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-phenyl-3-piperidinecarboxamide

HRID 2367295
Notes
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Reaction equation

HRID 2367295 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[C@H:15]([CH3:16])[CH2:14][CH2:13][C@H:12]([C:17]([OH:19])=O)[CH2:11]2)[CH:3]=1.CCN(C(C)C)C(C)C.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[C@H:15]([CH3:16])[CH2:14][CH2:13][C@H:12]([C:17]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:19])[CH2:11]2)[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51356007(3S,6R)-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid

Product 1

HCID 51357695
(3S,6R)-1-[6-Chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-phenyl-3-piperidinecarboxamide
Yield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3S,6R)-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (880 mg, 3.09 mmol) in CH2Cl2 (15 mL) at room temperature was added Hunig's base (1.62 mL, 9.27 mmol, 3 equiv) and aniline (0.56 mL, 6.18 mmol, 2 equiv), and the resulting mixture was chilled in an ice bath. To this stirred solution was added HATU (1.29 g, 3.40 mmol, 1.1 equiv) in one portion. The resulting suspension was stirred in the ice bath for 45 minutes. LCMS showed conversion complete. The mixture was filtered, and the filtrate was concentrated in vacuo. Silica gel column chromatography with gradient elution of 1% EtOAc in CHCl3 to 35% EtOAc in CHCl3 gave 700 mg of the title compound. LC-MS (ES) m/z=360 [M+H]+.

Workup

  1. temperaturethe resulting mixture was chilled in an ice bath
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. washSilica gel column chromatography with gradient elution of 1% EtOAc in CHCl3 to 35% EtOAc in CHCl3

Sources & evidence

ORD record
ord-db3a02464d894e5dbca60127f54bc641
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08697685B2

Reaction notes

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