Diisopropylethylamine → HCID 86710203, compound

HRID 2168199Notes

Reaction equation

HRID 2168199 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][N:13]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1>[CH3:12][N:13]([CH:21]1[CH2:22][CH2:23][N:24]([C:2]2[C:3]3[C:10]([CH3:11])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:25][CH2:26]1)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 86710203HCID 86710203, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine D4 (1 g), 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (1.918 g, 8.95 mmol, commercially available from e.g. Fluorochem, Apollo or Butt Park) and N,N-diisopropylethylamine (2.61 mL, 14.92 mmol) was heated at 150° C. for 20 minutes. LC/MS showed incomplete reaction. Further NMP (2 mL) and DIPEA (1.3 mL) was added. The mixture was heated at 150° C. for 20 minutes. The mixture was partitioned between ethyl acetate (70 mL) and water (60 mL) and the organic phase washed with water (2×60 mL) and brine (50 mL). It was dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by silica chromatography, eluting 50-100% EtOAc in isohexane. The desired fractions collected and the solvent has been evaporated to give the desired product D22 in 0.793 g as a white solid. LCMS [M+H][email protected] min (2 min run)

Workup

  1. customreaction
  2. customThe mixture was partitioned between ethyl acetate (70 mL) and water (60 mL)
  3. washthe organic phase washed with water (2×60 mL) and brine (50 mL)
  4. dry with materialIt was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by silica chromatography
  8. washeluting 50-100% EtOAc in isohexane
  9. customThe desired fractions collected
  10. customthe solvent has been evaporated

Sources & evidence

ORD record
ord-18af2e090b904881a8d0e489a8bcf01a
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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