Water → HCID 11501854, compound

HRID 1921912Notes

Reaction equation

HRID 1921912 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:19]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:16])[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylateHCID 59186792HCID 59186792, compound

Product 1

HCID 11501854HCID 11501854, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
86 °C

Procedure

To a solution of 4-methylaminomethylpiperidine-1-carboxylic acid tert-butyl ester (41 mg, 0.18 mmol) in anhydrous DMF (3 mL) was added 4-bromo-2-pyridin-4-yl-pyrimidine (Preparation 1, 42 mg, 0.18 mmol) and DIPEA (63 μL, 0.36 mmol), then the resulting solution was heated to 86° C. (bath) for 6 h. The reaction mixture was cooled to 20° C., then H2O (20 mL) and EtOAc (10 mL) were added. The layers were separated then the aqueous phase was extracted with EtOAc (2×30 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (EtOAc) gave the title compound: RT=2.87 nm in; m/z (ES+)=384 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×30 mL)
  4. washThe combined organics were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fcc2aa21ff44782ba97415c0c57c7e1
Source dataset
uspto-grants-2012_05
Patent number
US08173807B2

Reaction notes

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