Ammonium formate → HCID 22636101, compound

HRID 2415702Notes

Reaction equation

HRID 2415702 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([C:13]([NH:15][C:16]2[CH:17]=[C:18]([CH:31]=[CH:32][C:33]=2[CH3:34])[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:30])[CH3:29])[CH:23]=2)=[O:20])=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:30][N:28]([CH3:29])[C:24]1[CH:23]=[C:22]([NH:21][C:19](=[O:20])[C:18]2[CH:31]=[CH:32][C:33]([CH3:34])=[C:16]([NH:15][C:13](=[O:14])[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:36][CH:35]=3)[CH:17]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22636107HCID 22636107, compound

Product 1

HCID 22636101HCID 22636101, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Using an analogous procedure to that described in the last paragraph of the portion of Example 1 which is concerned with the preparation of starting materials, a mixture of 3-(4-benzyloxybenzamido)-N-(3-dimethylaminophenyl)4-methylbenzamide (0.227 g), 10% palladium-on-carbon (0.028 g), ammonium formate (0.37 g) and methanol (20 ml) was stirred and heated to reflux for 1.5 hours. The mixture was cooled to ambient temperature and filtered through diatomaceous earth. The filtrate was evaporated and the residue was triturated under water. The resultant solid was washed with a 100:1:0.12 mixture of methylene chloride, methanol and a saturated aqueous ammonium hydroxide solution and dried under vacuum at 55° C. There was thus obtained the title compound as a solid (0.104 g); NMR Spectrum: (DMSOd6) 2.26 (s, 3H), 2.84 (s, 6H), 6.44 (d, 1H), 6.84 (d, 2H), 7.13 (m, 3H), 7.39 (d, 1H), 7.76 (d, 1H), 7.86 (d, 2H), 7.92 (s, 1H), 9.73 (s, 1H), 9.91 (s, 1H); Mass Spectrum: M+H+ 391.

Workup

  1. customis concerned with the preparation of starting materials
  2. temperatureheated
  3. temperatureto reflux for 1.5 hours
  4. filtrationfiltered through diatomaceous earth
  5. customThe filtrate was evaporated
  6. customthe residue was triturated under water
  7. washThe resultant solid was washed with a 100:1:0.12 mixture of methylene chloride, methanol
  8. dry with materiala saturated aqueous ammonium hydroxide solution and dried under vacuum at 55° C

Sources & evidence

ORD record
ord-376d623d655e405e89a1db3e417f51ee
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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