Ammonium formate → HCID 15956333, compound

HRID 724960Notes

Reaction equation

HRID 724960 reaction equation
Br[C:2]1[C:12](Cl)=[N:11][C:10]2[N:9]([CH2:14][CH3:15])[C:8]3[N:16]=[CH:17][C:18]([CH:20]=[CH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][C:7]=3[C:6](=[O:28])[NH:5][C:4]=2[C:3]=1[CH3:29].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:14]([N:9]1[C:8]2[N:16]=[CH:17][C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][C:7]=2[C:6](=[O:28])[NH:5][C:4]2[C:3]([CH3:29])=[CH:2][CH:12]=[N:11][C:10]1=2)[CH3:15]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 86751841HCID 86751841, compound

Product 1

HCID 15956333HCID 15956333, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-phenylethen-1-yl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.22 g) was dissolved in 20 mL of methanol, and ammonium formate (2.0 g) and 10% palladium on carbon (0.13 g) were added. The reaction mixture was stirred at room temperature under argon for 6 d. Additional ammonium formate (1.5 g) was added, and the reaction mixture was stirred for an additional 2 d. The reaction mixture was filtered and diluted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated to give 98 mg of the title compound, which was recrystallized from ethyl acetate/isopropyl ether, to give 51 mg, m.p. 174°-175° C.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 d
  2. filtrationThe reaction mixture was filtered
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0248811ba7b4e38bfffcd5a90881877
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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