Ammonium formate → HCID 10143516, compound

HRID 2300236Notes

Reaction equation

HRID 2300236 reaction equation
C([N:8]([CH:27]1[CH2:31][CH2:30][N:29]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH2:28]1)[CH2:9][CH:10]([OH:26])[CH2:11][O:12][C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:42]([O:41][C:38]1[CH:39]=[CH:40][C:35]([S:32]([N:29]2[CH2:30][CH2:31][CH:27]([NH:8][CH2:9][C@H:10]([OH:26])[CH2:11][O:12][C:13]3[C:25]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[NH:18][C:17]=4[CH:16]=[CH:15][CH:14]=3)[CH2:28]2)(=[O:34])=[O:33])=[CH:36][CH:37]=1)[CH2:43][CH2:44][CH3:45]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12114485HCID 12114485, compound

Product 1

HCID 10143516HCID 10143516, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-{Benzyl-[1-(4-butoxy-benzenesulfonyl)-pyrrolidin-3-yl]-amino}-3-(9H-carbazol-4-yloxy)-propan-2-ol (0.19 g, 0.3 mmol) in methanol (2 ml) was added ammonium formate (0.29 g, 4.5 mmol), and 45 mg of 10% Pd/C. The mixture was stirred at reflux for 18 h. After cooling to room temperature, it was filtered through Celite. The solvent was evaporated and the residue triturated with ether-hexanes to give 0.15 g of a white solid; m.p. 118-119° C.; MS (ES) m/z 538.1 (MH+).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationit was filtered through Celite
  3. customThe solvent was evaporated
  4. customthe residue triturated with ether-hexanes

Sources & evidence

ORD record
ord-9b1d282b600f483f91c5bad4a35ef1e7
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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