Dimethylamine → HCID 69131080, compound

HRID 2253273Notes

Reaction equation

HRID 2253273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:36])[NH:32][C:33]([NH2:35])=[O:34])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:13]([OH:15])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:37](N1C=CN=C1)([N:39]1C=CN=[CH:40]1)=O.CNC.C1COCC1>CN(C=O)C.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:36])[NH:32][C:33]([NH2:35])=[O:34])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:13]([N:39]([CH3:40])[CH3:37])=[O:15])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 69130617HCID 69130617, compound

Product 1

HCID 69131080HCID 69131080, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6 (1.68 g, 3.43 mmol) in dry DMF (30 mL) was added carbonyldiimidazole (1.1 g, 6.86 mmol), and the reaction mixture was heated to 60° C. for 1 hr. The reaction mixture was cooled to 0° C. and a solution of dimethylamine in THF (2 M, 8.6 mL, 17.2 mmol) was added and stirred for 18 hr. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic phase was then rinsed sequentially with 10% citric acid (2×50 mL), water (2×50 mL), and brine (20 mL), then dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography using hexane-ethyl acetate (3:7) containing 1% acetic acid. Yield: 1.77 g, 100%.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic phase was then rinsed sequentially with 10% citric acid (2×50 mL), water (2×50 mL), and brine (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. additioncontaining 1% acetic acid

Sources & evidence

ORD record
ord-1b38626480b04950b542d038378cf32a
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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