Ammonium formate → HCID 24758040, compound

HRID 2425465Notes

Reaction equation

HRID 2425465 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)([OH:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH:17]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:23]2[C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:16]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58172477HCID 58172477, compound

Product 1

HCID 24758040HCID 24758040, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Compound 3 (2.4 g, 7.8 mmol), 1.5 g ammonium formate (23.8 mmol) and 20% Pd(OH)2/C (240 mg) were combined in MeOH (50 ml) and warmed to reflux for 2 hours. The mixture was cooled, filtered, concentrated and re-dissolved in MeOH. Filtration over 25 g SCX-2 (MeOH followed by 1 N NH3/MeOH) gave the title compound (1.5 g, 6.9 mmol, 88%) as amorphous material. 1H-NMR (400 MHz, D6DMSO): δ 11.3 (bs, 1H), 8.17-8.13 (m, 2H), 7.24 (s, 1H), 7.0-6.95 (m, 1H), 3.0-2.89 (m, 2H), 2.85 (d, J=13 Hz, 1H), 2.6-2.51 (m, 1H), 2.06-1.8 (m, 3H), 1.5-1.42 (m, 1H). (TLC MeOH/triethylamine (97/3 Rf 0.16).

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionre-dissolved in MeOH
  7. filtrationFiltration over 25 g SCX-2 (MeOH followed by 1 N NH3/MeOH)

Sources & evidence

ORD record
ord-a74a44be2fe04149af7ab4faf7727d00
Source dataset
uspto-grants-2011_06
Patent number
US07964728B2

Reaction notes

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