Ammonium formate → HCID 68180984, compound

HRID 538688Notes

Reaction equation

HRID 538688 reaction equation
C([CH:8]([CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][NH:31]1)[CH2:9][N:10]([C:20]1[CH:29]=[CH:28][C:23]2[O:24][CH2:25][CH2:26][O:27][C:22]=2[CH:21]=1)[CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO>[O:24]1[CH2:25][CH2:26][O:27][C:22]2[CH:21]=[C:20]([N:10]([CH:11]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12]3)[CH2:9][CH2:8][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][NH:31]3)[CH:29]=[CH:28][C:23]1=2

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 68180868HCID 68180868, compound

Product 1

HCID 68180984HCID 68180984, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of compound 59 (1.55 g, 3 31 mmol) in methanol (30 mL) was added HCOONH4 (2.08 g, 33.11 mmol) and the solution was purged with nitrogen for 30 minutes. 10% Pd—C (0.4 g) was then added and the solution was refluxed for 6 hours. The reaction mixture was filtered through Celite® reagent and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide compound 60.

Workup

  1. customthe solution was purged with nitrogen for 30 minutes
  2. addition10% Pd—C (0.4 g) was then added
  3. temperaturethe solution was refluxed for 6 hours
  4. filtrationThe reaction mixture was filtered through Celite® reagent
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe solution was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d282ae91bc154dde9d26998662728e5f
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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