1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-vinyloxyethoxy)-amide

HRID 2102399Notes

Reaction equation

HRID 2102399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([F:22])=[C:11]3[N:20]=[CH:19][N:18]([CH3:21])[C:12]3=[N:13][C:14]=2[C:15]([OH:17])=O)=[C:4]([F:23])[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:45]([O:47][CH2:48][CH2:49][O:50][NH2:51])=[CH2:46]>CCOC(C)=O>[CH:45]([O:47][CH2:48][CH2:49][O:50][NH:51][C:15]([C:14]1[N:13]=[C:12]2[N:18]([CH3:21])[CH:19]=[N:20][C:11]2=[C:10]([F:22])[C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:23])=[O:17])=[CH2:46]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamineHCID 69006569HCID 69006569, compound

Product 1

HCID 865996086-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-vinyloxyethoxy)-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (1.00 equivalent) and HOBt (1.50 equivalents) is added EDCI (1.50 equivalents) at room temperature. After stirring for 1 hour, O-(2-vinyloxy-ethyl)-hydroxylamine (1.10 equivalents) and TEA (1.20 equivalents) are added. The reaction mixture is stirred for 1 hour and diluted with EtOAc. The resulting mixture is washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give the crude material that is used directly without further purification.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour
  2. washThe resulting mixture is washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dc09f4daf294f44aa2fd79de7871da8
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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