Ammonium formate → HCID 57559224, compound

HRID 1723701Notes

Reaction equation

HRID 1723701 reaction equation
C([N:8]1[CH2:12][C@H:11]([N:13]2[CH2:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][C:14]2=[O:21])[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:20][C:17]1([F:19])[CH2:18][N:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])[C:14](=[O:21])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66606366HCID 66606366, compound

Product 1

HCID 57559224HCID 57559224, compoundYield 4,175.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of Step 9 (2 g, 0.06 mmol) in methanol was added excess ammonium formate and 10% Pd/C. The reaction mixture was heated under reflux overnight. After filtering, the solution was evaporated and residue was purified on silica gel (10% methanol/chloroform) to obtain the title product (800 mg). 1H NMR (400 MHz, CDCl3) δ 5.25 (1H,s), 4.7 (1H, m), 3.45 (1H, m), 3.25 (1H, m), 3.04 (m) 2.9 (1H, m), 2.5 (6H, m), 1.80 (4H, m), 1.45 (9H, s). MS m/z 284 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationAfter filtering
  4. customthe solution was evaporated
  5. customresidue was purified on silica gel (10% methanol/chloroform)

Sources & evidence

ORD record
ord-09a992bc23f74de1b847c3d9aa53f007
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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