Ethylacetate methanol → 798577-91-0

HRID 2405031Notes

Reaction equation

HRID 2405031 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:38])[CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[C:28]2[C:32]([NH:33][CH2:34][CH2:35][C:36]#[N:37])=[N:31][O:30][N:29]=2)=[CH:13][CH:12]=1)C1C=CC=CC=1.C(OCC)(=O)C.CO>C(OCC)(=O)C.CO.[Pd]>[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:38])[CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[C:28]2[C:32]([NH:33][CH2:34][CH2:35][C:36]#[N:37])=[N:31][O:30][N:29]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 21584119Ethylacetate methanolHCID 70792370HCID 70792370, compound

Product 1

HCID 11176685798577-91-0Yield 73.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6.4 g of [4-(2-{2-[4-(2-cyano-ethylamino)-furazan-3-yl]-benzoimidazol-1-yl}-acetyl)-phenyl]-carbamic acid benzyl ester (12.3 mmol, 1 eq) in a mixture of 700 ml of ethyl acetate and 500 ml of methanol are added 1.3 g of 10% palladium on carbon. The reaction mixture is stirred for 3 h under hydrogen atmosphere (1 atm) at room temperature. Then it is filtered through celite and concentrated under reduced pressure to give the crude product as a light yellow solid, which is suspended in 60 ml of a 7/5 ethyl acetate/methanol mixture. Filtration provides 3.5 g of the desired product as off-white solid. The filtrate is concentrated and the residue is treated as above with 5 ml of the 7/5 ethyl acetate/methanol mixture. Filtration gives 0.45 g of a second crop of the product.

Workup

  1. filtrationThen it is filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customto give the crude product as a light yellow solid, which
  4. filtrationFiltration

Sources & evidence

ORD record
ord-8e3c78171ae14c9ca40e35ab99b862b7
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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