Ammonium formate → HCID 54583742, compound

HRID 2077037Notes

Reaction equation

HRID 2077037 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:18][CH2:17][C:16]2[C:19](Cl)=[N:20][C:21]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:22][C:15]=2[CH2:14][CH2:13]1)C1C=CC=CC=1>[Pd].CO>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][C:21]1[N:20]=[CH:19][C:16]2[CH2:17][CH2:18][NH:12][CH2:13][CH2:14][C:15]=2[N:22]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59312350HCID 59312350, compound

Product 1

HCID 54583742HCID 54583742, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (112 mg, 1.78 mmol) and 10% palladium on carbon (27 mg, 0.27 mmol) was added to a solution of 7-benzyl-4-chloro-2-(2-fluorobenzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine the product of Preparation 31, Step B, (136 mg, 0.36 mmol) in methanol (12 ml) and heated to reflux for 5 h. The reaction mixture was filtered through Arbocel, the filtrate concentrated in vacuo and the residue purified by HPLC (Phenomenex column, acetonitrile:water:formic acid gradient) to afford the title compound as a colourless oil in 11.5% yield, 10.5 mg.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. filtrationThe reaction mixture was filtered through Arbocel
  4. concentrationthe filtrate concentrated in vacuo
  5. customthe residue purified by HPLC (Phenomenex column, acetonitrile:water:formic acid gradient)

Sources & evidence

ORD record
ord-da58195268ac4dc39a5fd72a47746cd6
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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