Hydrochloric Acid → HCID 66926116, compound

HRID 2405037Notes

Reaction equation

HRID 2405037 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:48])[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][C:34](=[O:47])[CH2:35][NH:36]C(OCC3C=CC=CC=3)=O)=[N:31][O:30][N:29]=2)=[CH:13][CH:12]=1)C1C=CC=CC=1.[ClH:50].O1CCOCC1>O1CCCC1.CO.[Pd]>[ClH:50].[NH2:36][CH2:35][C:34]([NH:33][C:32]1[C:28]([C:20]2[N:19]([CH2:18][C:17]([C:14]3[CH:15]=[CH:16][C:11]([NH2:10])=[CH:12][CH:13]=3)=[O:48])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=2)=[N:29][O:30][N:31]=1)=[O:47]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70792421HCID 70792421, compound

Product 1

HCID 66926116HCID 66926116, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.2 g of [4-(2-{2-[4-(2-benzyloxycarbonylamino-acetylamino)-furazan-3-yl]-benzoimidazol-1-yl}-acetyl)-phenyl]-carbamic acid benzyl ester (0.29 mmol; 1 eq.) in 2 mL of tetrahydrofuran and 2 mL of methanol containing 0.19 mL of a solution of 4M HCl in 1,4-dioxane (0.86 mmol; 3 eq.) and 0.046 g of 10% Pd/C (0.04 mmol; 0.14 eq.) is stirred for 7 hours under hydrogen atmosphere at room temperature. Then the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is suspended in 2 mL of a mixture of dichloromethane/diisopropylether (1/1, v/v) and the suspension is filtered. The solid is washed with 2 mL of diisopropylether and dried under reduced pressure to give the crude product. The solid is purified by MCI gel column chromatography (eluent water/acetonitrile=75/25 to 65/35, containing 0.1% of HCl) to afford 0.02 g of the desired product as a light brown powder.

Workup

  1. filtrationThen the mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. filtrationv/v) and the suspension is filtered
  4. washThe solid is washed with 2 mL of diisopropylether
  5. customdried under reduced pressure
  6. customto give the crude product
  7. customThe solid is purified by MCI gel column chromatography (eluent water/acetonitrile=75/25 to 65/35, containing 0.1% of HCl)

Sources & evidence

ORD record
ord-668bf68beea54b28b6b8f8be79b2ecb6
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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