Hydrochloric Acid → HCID 70872103, compound

HRID 2405033Notes

Reaction equation

HRID 2405033 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:34])[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]([NH2:33])=[N:31][O:30][N:29]=2)=[CH:13][CH:12]=1)(C)(C)C.[ClH:37].C(OC(C)C)(C)C>O1CCOCC1>[ClH:37].[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:34])[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]([NH2:33])=[N:31][O:30][N:29]=2)=[CH:15][CH:16]=1)=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 70792365HCID 70792365, compound

Product 1

HCID 70872103HCID 70872103, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 0.045 g of [(4-{2-[2-(4-amino-furazan-3-yl)-benzoimidazol-1-yl]-acetyl}-phenylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (0.09 mmol; 1 eq.) in 0.5 mL of 1,4-dioxane are added dropwise 0.11 mL of a 4M HCl solution in 1,4-dioxane (0.44 mmol; 5 eq.) at room temperature. The reaction mixture is stirred for 2 h at room temperature. Then, 5 mL of diisopropylether are added and the resulting suspension is filtered, washed with diisopropylether (2×2 mL) and dried under reduced pressure to give 0.04 g of crude material. The crude solid is subjected to MCI gel column chromatography eluting with a mixture water/acetonitrile (85/15 to 70/30) containing 0.05% of HCl, to afford 0.014 g of the desired product as an orange powder.

Workup

  1. filtrationthe resulting suspension is filtered
  2. washwashed with diisopropylether (2×2 mL)
  3. customdried under reduced pressure
  4. customto give 0.04 g of crude material
  5. washeluting with a mixture water/acetonitrile (85/15 to 70/30)
  6. additioncontaining 0.05% of HCl

Sources & evidence

ORD record
ord-91d81a40a7714c2782ff264e94c66670
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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