Ammonium formate → HCID 20634980, compound

HRID 460387Notes

Reaction equation

HRID 460387 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44]CC6C=CC=CC=6)=[C:38]([O:52][CH3:53])[CH:37]=5)=[CH:32][N:31]=4)[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[O:54][CH3:55])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:29][CH2:28][CH2:27][N:26]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[C:40]([O:42][CH3:43])[C:39]([OH:44])=[C:38]([O:52][CH3:53])[CH:37]=5)=[CH:32][N:31]=4)[CH2:25][CH2:24]3)=[N:21][CH:22]=2)=[CH:11][C:10]=1[O:54][CH3:55]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 20634971HCID 20634971, compound

Product 1

HCID 20634980HCID 20634980, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1,4-bis[5-(4-benzyloxy-3,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine (27.0 mg, 0.037 mmol) in methanol (1.0 mL) were added 10% palladium on charcoal (14.0 mg) and ammonium formate (14.0 mg, 0.220 mmol), and the resulting mixture was stirred at 70° C. for 2 hours. 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 water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from methanol-chloroform-diethyl ether to yield the title compound as pale brown needles (melting point: 200.0–202.0° C.) (17.0 mg, yield: 85%).

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 water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol-chloroform-diethyl ether

Sources & evidence

ORD record
ord-ccfa9fa390924c4292c5f6d23805eacf
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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