Triethylamine → HCID 59834743, compound

HRID 271578Notes

Reaction equation

HRID 271578 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.[N:25]1([CH2:30][CH2:31][CH2:32][NH2:33])[CH:29]=[CH:28][N:27]=[CH:26]1.C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO.CC(C)=O>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:33][CH2:32][CH2:31][CH2:30][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH2:18][CH2:17]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 787361H-Imidazole-1-propanamineHCID 4311764Sodium borohydrideHCID 9880368HCID 9880368, compound

Product 1

HCID 59834743HCID 59834743, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the mixture of 100 mg (0.30 mmoles) of 7-(2,2-dimethyl-propyl)-6-(4-oxo-piperidin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile, 60 mg (0.48 mmoles) of 3-Imidazol-1-yl-propylamine and 0.15 ml (1.1 mmoles) of triethylamine in 5 ml of CH2Cl2, 58 mg (1.1 mmoles) of MgSO4 is added at ambient temperature. The mixture is stirred for 15.5 hours at ambient temperature. The reaction mixture is filterlated to remove MgSO4 and concentrated under reduced pressure to give crude imine. To a solution of crude imine in 5 ml of MeOH, 13 mg (0.33 mmoles) of NaBH4 is added at −10-−20° C., and the reaction mixture is stirred at 0° C. for 4.5 hours. After addition of 5 ml of acetone, the mixture is concentrated, diluted with H2O, and then extracted with CH2Cl2. The combined extrats are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 95 mg of desired 7-(2,2-dimethyl-propyl)-6-[4-(3-imidazol-1-yl-propylamino)-piperidin-1-ylmethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 73% yield.

Workup

  1. additionis added at ambient temperature
  2. customto remove MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give crude imine
  5. stirringthe reaction mixture is stirred at 0° C. for 4.5 hours
  6. concentrationthe mixture is concentrated
  7. additiondiluted with H2O
  8. extractionextracted with CH2Cl2
  9. washThe combined extrats are washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2abdab5832ff42f3a473b11f0f481540
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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