Dimethylamine → HCID 59259013, compound

HRID 641641Notes

Reaction equation

HRID 641641 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:17][CH2:18][CH3:19])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8]([CH2:20][CH2:21][C:22]([OH:24])=O)[C:7]2=[O:25])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][NH:27][CH3:28].C(N(CC)CC)C>CN(C=O)C>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:17][CH2:18][CH3:19])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8]([CH2:20][CH2:21][C:22]([N:27]([CH3:28])[CH3:26])=[O:24])[C:7]2=[O:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 59258938HCID 59258938, compound

Product 1

HCID 59259013HCID 59259013, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-(8-cyclopentyl-2-(ethylamino)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)propanoic acid (94 mg, 0.27 mmole), dimethylamine (1.09 mmole, 0.55 ml of 2.0 M solution in THF), triethylamine (27.6 mg, 0.27 mmole), O-(7-Azabenzotriazole-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU, 104 mg, 0.27 mmole) and DMF (3.0 ml) were added to a reaction vial equipped with a stir bar. The reaction mixture was heated at 50° C. for 26 h. The reaction was quenched with water (2 ml), and the volatiles were removed under reduced pressure to a residue. Ethyl acetate (70 ml) and water (30 ml) were added and shaken well. The organic layer was separated, washed with water (2×30 ml), brine (30 ml), and dried over sodium sulfate. The solvent was removed under reduced pressure to a residue, which was purified using silica (100% petroleum ether to 100% ethyl acetate). The fractions were combined, and the volatiles were removed to a colorless oil as the title compound (55 mg, 54% yield).

Workup

  1. customvial equipped with a stir bar
  2. customThe reaction was quenched with water (2 ml)
  3. customthe volatiles were removed under reduced pressure to a residue
  4. additionEthyl acetate (70 ml) and water (30 ml) were added
  5. customThe organic layer was separated
  6. washwashed with water (2×30 ml), brine (30 ml)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure to a residue, which
  9. customwas purified

Sources & evidence

ORD record
ord-46097e4960d542cda643d12eccb7b214
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

Loading…