Ammonium formate → HCID 10500121, compound

HRID 1596367Notes

Reaction equation

HRID 1596367 reaction equation
C(OC([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([N:29]2[CH2:35][CH:34]3[CH2:36][CH2:37][CH:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:28])[C:13]1=[O:38])=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C.C(OCC)(=O)C>[NH2:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([N:29]2[CH2:35][CH:34]3[CH2:33][CH2:32][CH:31]([CH2:37][CH2:36]3)[CH2:30]2)=[O:28])[C:13]1=[O:38]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 10506033HCID 10506033, compound

Product 1

HCID 10500121HCID 10500121, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-1-[(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl]-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one (1.23 g), 10% palladium on carbon (50% wet, 250 mg) and ammonium formate (600 mg) in ethanol (15 ml) was stirred at room temperature for 1 hour. The catalyst was filtered off and the filtrate was evaporated in vacuo to afford a residue, which was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine successively. After drying over sodium sulfate, the solvent was evaporated in vacuo to afford a residue, which was triturated in diisopropyl ether and collected by filtration to give (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one (792 mg, 87.0% yield) as a crystalline powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto afford a residue, which
  4. washwashed with saturated aqueous sodium bicarbonate, water and brine successively
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customto afford a residue, which
  8. customwas triturated in diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-890a4df891dc4f91b5f31d991022d65f
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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