Ammonium formate → HCID 22330112, compound

HRID 586394Notes

Reaction equation

HRID 586394 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]([O:33]CC3C=CC=CC=3)=[O:32])[CH2:26][CH2:25]2)[CH:19]=1)[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[O:8])([O-])=O.C([O-])=O.[NH4+]>O1CCCC1.CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:26][CH2:25]2)[CH:19]=1)[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[O:8]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22330062HCID 22330062, compound

Product 1

HCID 22330112HCID 22330112, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxyethyl 3-nitro-4-(3-(4-(benzyloxy-carbonyl-methyl)-1-piperazinyl)-phenylamino)-benzoate (3d) (3.5 g; 6.4 mmol) in a mixture of tetrahydrofurane (50 ml) and DMF (5 ml) was added palladium catalyst (0.9 g, 5% Pd on activated carbon) and ammonium formiate (0.8 g; 12.6 mmol) and the mixture was heated to reflux for 2 hours. The cooled mixture was filtered through celite and the solvent was removed under reduced pressure to leave 2d, quantitatively.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe cooled mixture was filtered through celite
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e491736785f44c9cb362a914d8b10c9a
Source dataset
uspto-grants-2005_08
Patent number
US06936613B2

Reaction notes

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