Ammonium formate → HCID 10705894, compound

HRID 1274124Notes

Reaction equation

HRID 1274124 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]([C:9]1[C:14]([NH2:15])=[N:13][C:12]([NH:16][CH:17]2[CH2:22][CH2:21][N:20](CC3C=CC=CC=3)[CH2:19][CH2:18]2)=[C:11](Cl)[N:10]=1)=[O:8]>C(O)C>[CH3:5][O:6][C:7]([C:9]1[C:14]([NH2:15])=[N:13][C:12]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:11][N:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 10571539HCID 10571539, compound

Product 1

HCID 10705894HCID 10705894, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ammonium formate (3.5 g, 48 mmol) was added to a solution of (37) (1.8 g, 4.8 mmol) in 60 mL of absolute ethanol. The mixture was purged with argon then palladium (0.5 g, 5% on activated carbon) was added. The resulting mixture was heated at 80° C. for with argon then palladium (0.5 g, 5% on activated carbon) was added. The resulting mixture was heated at 80° C. for 12 h then was cooled to 25° C. and filtered through celite. The filtrate was concentrated in vacuo and the residue was cooled to 0° C. Saturated Na2CO3 (100 mL) was added, and the resulting mixture was stirred for 30 min. The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give 1.3 g (quantitative yield) of the title compound: TLC (Rf =0.24; 10% MeOH/CH2Cl2); 1H NMR (DMSO) δ 7.86 (d, 1H, J=6.9), 7.28 (s, 1H), 7.10 (br s, 2H), 3.95 (m, 1H), 3.69 (s, 3H), 3.26 (d, 2H, J=12.8), 2.92 (t, 2H, J=9.8), 2.00 (d, 2H, J=12.0), 1.70 (m, 2H); 13C NMR (DMSO) δ 167.0, 156.4, 154.6, 122.8, 109.8, 50.9, 44.4, 41.8, 27.9; HRMS (FAB) m/z 252.1466 (M+H)+ (C11H17N5O2 requires 252.1461).

Workup

  1. customThe mixture was purged with argon
  2. additionpalladium (0.5 g, 5% on activated carbon) was added
  3. additionpalladium (0.5 g, 5% on activated carbon) was added
  4. temperatureThe resulting mixture was heated at 80° C. for 12 h
  5. temperaturethen was cooled to 25° C.
  6. filtrationfiltered through celite
  7. concentrationThe filtrate was concentrated in vacuo
  8. temperaturethe residue was cooled to 0° C
  9. additionSaturated Na2CO3 (100 mL) was added
  10. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  11. dry with materialthe combined organic layers were dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ac9c0ca49cf405d933326e28aff863e
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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