Ethyl diazoacetate → HCID 71117301, compound

HRID 629915Notes

Reaction equation

HRID 629915 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9](/[CH:13]=[CH:14]/[CH3:15])=[CH:10][CH:11]=2)[N:6]([CH3:16])[C:5]1=[O:17].[N+](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-]>C1(C)C=CC=CC=1>[CH3:18][C:2]([CH3:1])([CH3:19])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH:13]3[CH:14]([CH3:15])[CH:22]3[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:10][CH:11]=2)[N:6]([CH3:16])[C:5]1=[O:17]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 71136229HCID 71136229, compound

Product 1

HCID 71117301HCID 71117301, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-(2,2-Dimethylpropyl)-3-methyl-5-[(1E)-prop-1-en-1-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (33-1, 600 mg, 2.3 mmol, 1.0 equiv) was added to anhydrous toluene (4.8 mL). Ethyl diazoacetate (720 μL, 6.9 mmol, 3.0 equiv) was added and the resulting solution was heated to 100° C. for 18 h. Following this duration, LCMS showed complete consumption of 33-1. The reaction mixture was diluted with ethyl acetate (50 mL) and saturated NaHCO3 (25 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. Purification by normal-phase HPLC (0-40% EtOAc:hexanes) provided 33-2 as a white solid. MS m/z (M+H): calculated=346.2127; observed=346.2134.

Workup

  1. customconsumption of 33-1
  2. additionThe reaction mixture was diluted with ethyl acetate (50 mL) and saturated NaHCO3 (25 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an orange oil
  9. customPurification by normal-phase HPLC (0-40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-5cdb604461044ba3af5995850fdb9c07
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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