Dimethylformamide → HCID 22744289, compound

HRID 47862Notes

Reaction equation

HRID 47862 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][CH:12]([N:15]([C:17]4[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=4)[CH3:16])[C:9]=3[CH:10]=2)[N:5]=[C:4]([CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[NH:3]1.[H-].[Na+].[CH3:39]N(C=O)C>>[CH3:39][N:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][CH:12]([N:15]([C:17]4[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=4)[CH3:16])[C:9]=3[CH:10]=2)[N:5]=[C:4]1[CH2:30][N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 135809779HCID 135809779, compound

Product 1

HCID 22744289HCID 22744289, compoundYield 91%

Procedure

To a solution of tert-butyl 4-[N-[4-oxo-2-(piperidin-1-yl)methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-methylamino]benzoate (0.060 g, 0.123 mmol) in anhydrous DMF (3 ml) under argon was added a dispersion of NaH in mineral oil (60% w/w) (0.0060 g, 0.147 mmol) and the reaction mixture was stirred for 1 min. Mel (15 μL, 0.246 mmol) was then added via syringe and the reaction mixture was stirred for a further 2 hours. The reaction mixture was then partitioned between a saturated aqueous solution of sodium bicarbonate (40 ml) and ethyl acetate (75 ml) and the organic phase was then successively washed with a saturated aqueous solution of sodium bicarbonate (30 ml), brine (30 ml), then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (0.056 g, 91%).

Workup

  1. additionMel (15 μL, 0.246 mmol) was then added via syringe
  2. stirringthe reaction mixture was stirred for a further 2 hours
  3. customThe reaction mixture was then partitioned between a saturated aqueous solution of sodium bicarbonate (40 ml) and ethyl acetate (75 ml)
  4. washthe organic phase was then successively washed with a saturated aqueous solution of sodium bicarbonate (30 ml), brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56c091b614ad4f72a840a216588345f8
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Reaction notes

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