4-N-Boc-4-N-Methyl-aminopiperidine → HCID 67988168, compound

HRID 2168190Notes

Reaction equation

HRID 2168190 reaction equation
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[CH3:11][N:12]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>C(O)C>[CH3:11][N:12]([CH:20]1[CH2:21][CH2:22][N:23]([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:24][CH2:25]1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 178418725HCID 178418725, compound

Product 1

HCID 67988168HCID 67988168, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

a mixture of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (307 mg, 2 mmol, commercially available from e.g. Aldrich, Apollo or Matrix) and 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (429 mg, 2.000 mmol, commercially available from e.g. Fluorochem, Astatech or Apollo)) in Ethanol (4 ml) was microwaved at 120° C. for 1 h on normal absorption. After evaporation of the solvent, the crude product was purified via MDAP using the High pH extended method. Fractions containing product from each MDAP were combined and evaporated to give D12 as a white solid in 158 mg. LCMS [M+H][email protected] min (2 min run)

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified via MDAP
  3. additionFractions containing product from each MDAP
  4. customevaporated
  5. customto give D12 as a white solid in 158 mg
  6. customLCMS [M+H][email protected] min (2 min run)

Sources & evidence

ORD record
ord-30bfbde949d84214b4c5adf6efb14395
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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