Diisopropylethylamine → HCID 59508976, compound

HRID 1020077Notes

Reaction equation

HRID 1020077 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[N:57]=[CH:56][N:55]=[C:54]([NH2:58])[CH:53]=1>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[N:57]=[CH:56][N:55]=[C:54]([NH:58][C:8]([CH:5]2[CH2:4][CH2:3][C:2](=[O:1])[NH:7][CH2:6]2)=[O:10])[CH:53]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5600906-Oxopiperidine-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59508976HCID 59508976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-oxo-piperidine-3-carboxylic acid (XLIX) (0.22 g, 1.5 mmol) in dry DMF (10 ml) was added HBTU (1.13 g, 2.98 mmol) and DIPEA (0.40 ml, 2.3 mmol) under ice cooled condition, and then it was allowed to stir at room temperature for 45 minutes. To this reaction mixture was added 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.30 g, 1.5 mmol) in dry DMF dropwise at ice bath temperature. The reaction mixture was then heated for 4 hours at 120° C. After completion of the reaction, it was cooled and DMF was evaporated completely. The residue was dissolved in ethyl acetate (30 ml), washed with water (2×15 ml) and brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. Final purification was achieved by flash column chromatography using silica gel (10% methanol/dichloromethane) to give 6-oxo-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]amide. Yield: 78.2 mg, 17%.

Workup

  1. temperatureThe reaction mixture was then heated for 4 hours at 120° C
  2. customAfter completion of the reaction, it
  3. temperaturewas cooled
  4. customDMF was evaporated completely
  5. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  6. washwashed with water (2×15 ml) and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customFinal purification

Sources & evidence

ORD record
ord-bf1e595ac53d4f378eb7ddcd96d6ad11
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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