Acetic Acid → HCID 11233069, compound

HRID 229361Notes

Reaction equation

HRID 229361 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:8]=[C:9]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=C(C=O)[N:10]2[CH:23]=1)=[O:5])[CH3:2].[C-]#N.[Na+].C(O)(=O)C.[C:31]([O:34][CH2:35]C)(=[O:33])[CH3:32]>CO.[O-2].[O-2].[Mn+4].CO.C(OCC)(=O)C>[CH3:35][O:34][C:31]([C:32]1[N:10]2[CH:23]=[C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[N:8]=[C:9]2[CH:14]=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)=[O:33]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 11232103HCID 11232103, compound

Product 1

HCID 11233069HCID 11233069, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
23 °C

Procedure

Activated manganese dioxide (600 mg) was added to a solution of the alcohol (12) (90 mg, 0.29 mmol) in a mixture of ethyl acetate (20 mL) and methanol (10 mL) and the mixture was stirred vigorously at 23° C. for 2 h. APCI-MS Found [M+H]=310. The reaction mixture was filtered through Celite, washing through with more ethyl acetate/methanol. The combined filtrates were concentrated to dryness to give the aldehyde, 1-Ethyl-3-(5-formyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea (13), which was used directly in the next step. To a solution of the crude aldehyde (13) in methanol (20 mL) was added NaCN (75 mg, 1.53 mmol) and acetic acid (26 μL, 0.46 mmol). Activated manganese dioxide (600 mg) was added last and the mixture was stirred at 23° C. for 3 h, then filtered through Celite, washing through with more methanol. The combined filtrates were concentrated to dryness to leave a solid which was adsorbed onto silica. Silica gel chromatography (ethyl acetate gradient to methanol/ethyl acetate (8:92)) provided 2-(3-Ethyl-ureido)-7-pyridin-3-yl-imidazo[1,2-a]pyridine-5-carboxylic acid methyl ester (14) (36 mg). HRFAB-MS Found: [M+H]=340.1413. C17H18N5O3 requires 340.1410.

Workup

  1. filtrationfiltered through Celite
  2. washwashing through with more methanol
  3. concentrationThe combined filtrates were concentrated to dryness
  4. customto leave a solid which

Sources & evidence

ORD record
ord-1d023a7e48a343e580b6fb8231c64a74
Source dataset
uspto-grants-2009_07
Patent number
US07563788B2

Reaction notes

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