Ammonium formate → HCID 57893734, compound

HRID 1822041Notes

Reaction equation

HRID 1822041 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[N:20]=[C:19]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3Cl)[CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]1([CH3:33])[CH3:32])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:32][C:9]1([CH3:33])[CH2:10][CH:11]([O:14][C:15]2[N:20]=[C:19]([NH:21][C:22](=[O:31])[C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57893667HCID 57893667, compound

Product 1

HCID 57893734HCID 57893734, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Combine N-[6-(1-benzyl-2,2-dimethyl-piperidin-4-yloxy)-pyridin-2-yl]-2-chloro-4-fluoro-benzamide (preparation 93, 0.056 g, 0.12 mmol), ethanol (5 mL), 10% palladium/carbon (0.01 g) and ammonium formate (0.064 g, 1.2 mmol), stir and heat to 80° C. After 16 hr., cool to ambient temperature. Filter through celite, rinsing with ethanol. Concentrate filtrate. Dissolve the residue in methanol (10 mL) and load on an SCX column (10 g); wash with methanol (2×50 mL); elute product with 2M ammonia/methanol (2×50 mL). Concentrate the eluent to obtain the title compound (0.042 g, 100%): Mass spectrum (electrospray): m/z=344.2 (M+1); 1H NMR (CDCl3): 8.2 (bs, 1H), 7.9 (m, 3H), 7.7 (m, 1H), 7.2 (m, 2H), 6.5 (d, 1H), 5.2 (m, 1H), 3.1 (m, 1H), 3.0 (m, 1H), 2.1 (m, 1H), 2.0 (dd, 1H), 1.5 (m, 2H), 1.25 (s, 6H).

Workup

  1. temperature, cool to ambient temperature
  2. filtrationFilter through celite
  3. washrinsing with ethanol
  4. dissolutionDissolve the residue in methanol (10 mL)
  5. washwash with methanol (2×50 mL)
  6. concentrationConcentrate the eluent

Sources & evidence

ORD record
ord-cc90840a8c424cf7ac3fe41a3ce14a09
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

Loading…