Formamide → HCID 9998494, compound

HRID 751304Notes

Reaction equation

HRID 751304 reaction equation
[CH:1]([NH2:3])=[O:2].[H-].[Na+].C(OC([C:11]1[N:15]2[CH:16]=[C:17]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:23][N:22]4[CH2:32][CH2:33][CH2:34][C:21]=34)[CH:18]=[CH:19][C:14]2=[N:13][CH:12]=1)=O)C>CN(C=O)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:31][C:27]1[N:26]=[C:25]([C:24]2[C:20]([C:17]3[CH:18]=[CH:19][C:14]4[N:15]([C:11]([C:1]([NH2:3])=[O:2])=[CH:12][N:13]=4)[CH:16]=3)=[C:21]3[CH2:34][CH2:33][CH2:32][N:22]3[N:23]=2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 713FormamideHCID 24758Sodium hydrideHCID 69203469HCID 69203469, compound

Product 1

HCID 9998494HCID 9998494, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
155 °C

Procedure

Add formamide (36 mL) to a suspension of sodium hydride (2.04 g, 60% dispersion in mineral oil, 51.1 mmol) and 6-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (3.6 g, 9.29 mmol) in DMF (15 mL) over 10 min. Heat at 155° C. for 40 min, cool, dilute with ethyl acetate, and carefully dilute with saturated aqueous sodium bicarbonate. Filter any un-dissolved solid and wash with ethyl acetate. Concentrate the remaining organic layer and adsorb onto a 1:1 mixture of SiO2 and Celite®. Flash chromatography using ethyl acetate methanol mixtures followed by trituration of the combined lots in diethyl ether gives the titled compound (3.32 g, 99%) as a white solid. TOF MS ES+ exact mass calculated for C10H9IN2O2 (p+1): m/z=359.1620 Found: 359.1617.

Workup

  1. temperaturecool
  2. filtrationFilter any un-dissolved solid
  3. washwash with ethyl acetate
  4. concentrationConcentrate the remaining organic layer
  5. additionadsorb onto a 1:1 mixture of SiO2 and Celite®

Sources & evidence

ORD record
ord-2d182e0570f24efc814c0bacdf9236b8
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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