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Triethylamine → (5-Chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazine-1-yl}-pyridin-3-yl)-acetonitrile

HRID 2195031
Notes
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Reaction equation

HRID 2195031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:33]O)[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][CH:28]3[CH3:32])[N:15]=2)[CH2:10][CH2:9]1.C[CH2:36][N:37](CC)CC.CS(Cl)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:33][C:36]#[N:37])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([N:27]3[CH2:31][CH2:30][CH2:29][CH:28]3[CH3:32])[N:15]=2)[CH2:10][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11670243(5-Chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-yl)-methanol

Product 1

HCID 66838806(5-Chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazine-1-yl}-pyridin-3-yl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To an ice cooled solution of (5-chloro-6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyridin-3-yl)-methanol (136 mg, 0.282 mmol) and Et3N (79 μL, 0.564 mmol) in DCM, add MsCl (33 μL, 0.422 mmol) dropwise. Remove ice bath and stir for 1 h at room temperature. Dilute with 3 volumes of DCM, wash with brine, dry the organic layer (Na2SO4) and concentrate under reduced pressure. Dissolve the crude mesylate in DMSO, add 138 mg of NaCN and heat at 60° C. until no starting material remains as indicated by TLC. Dilute with water and extract the aqueous solution with EtOAc. Wash the organic extract with water (2×) followed by brine (1×), dry (Na2SO4) and concentrate under reduced pressure to give crude product. Purify using flash chromatography to give pure title compound.

Workup

  1. washwash with brine
  2. dry with materialdry the organic layer (Na2SO4)
  3. concentrationconcentrate under reduced pressure
  4. dissolutionDissolve the crude mesylate in DMSO
  5. additionadd 138 mg of NaCN
  6. temperatureheat at 60° C. until no starting material
  7. additionDilute with water
  8. extractionextract the aqueous solution with EtOAc
  9. washWash the
  10. extractionorganic extract with water (2×)
  11. dry with materialdry (Na2SO4)
  12. concentrationconcentrate under reduced pressure
  13. customto give crude product
  14. customPurify

Sources & evidence

ORD record
ord-ba3ea3c7ae8b47e99f0e7b44a7917bd5
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334382B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes