Hydrochloric Acid → HCID 20634926, compound

HRID 49305Notes

Reaction equation

HRID 49305 reaction equation
C(OC([NH:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([C:33]4[CH:38]=[CH:37][C:36]([C:39]5[CH:44]=[C:43]([O:45][CH3:46])[C:42]([NH:47]C(OCC6C=CC=CC=6)=O)=[C:41]([O:58][CH3:59])[CH:40]=5)=[CH:35][N:34]=4)[CH2:28][CH2:27]3)=[N:24][CH:25]=2)=[CH:14][C:13]=1[O:60][CH3:61])=O)C1C=CC=CC=1.[ClH:62].C(OCC)(=O)C.C(O)C>C(O)(=O)C.[Pd].C(Cl)(Cl)Cl>[ClH:62].[ClH:62].[ClH:62].[ClH:62].[NH2:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([C:33]4[CH:38]=[CH:37][C:36]([C:39]5[CH:44]=[C:43]([O:45][CH3:46])[C:42]([NH2:47])=[C:41]([O:58][CH3:59])[CH:40]=5)=[CH:35][N:34]=4)[CH2:28][CH2:27]3)=[N:24][CH:25]=2)=[CH:14][C:13]=1[O:60][CH3:61]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 20634972HCID 20634972, compound

Product 1

HCID 20634926HCID 20634926, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1,4-bis[5-(4-benzyloxycarbonylamino-3,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine (120.0 mg, 0.140 mmol) in acetic acid (2.0 mL) was added 10% palladium on charcoal (24.0 mg), and the resulting mixture was stirred at 50° C. for 1.5 hours under hydrogen. Insoluble materials were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. A solution of the residue in chloroform was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in chloroform (5.0 mL) a 4.0 M solution of hydrogen chloride in ethyl acetate (0.14 mL, 0.56 mmol), and the resulting mixture was concentrated under reduced pressure. Ethanol (5.0 mL) was added to the residue, and the resulting mixture was concentrated under reduced pressure. Diethyl ether was added to the residue, and the resulting precipitate was collected by filtration to yield the title compound as a pale brown amorphous powder (84.0 mg, yield: 82%).

Workup

  1. customInsoluble materials were removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washA solution of the residue in chloroform was washed with saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe resulting mixture was concentrated under reduced pressure
  7. additionDiethyl ether was added to the residue
  8. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-a0813cd016674920b603ebd8e4f372ef
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Reaction notes

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