Ammonium formate → HCID 10142908, compound

HRID 479961Notes

Reaction equation

HRID 479961 reaction equation
C([N:8]([CH:27]1[CH2:30][N:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[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]>[CH2:41]([O:40][C:37]1[CH:38]=[CH:39][C:34]([S:31]([N:29]2[CH2:28][CH:27]([NH:8][CH2:9][CH: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)[CH2:30]2)(=[O:33])=[O:32])=[CH:35][CH:36]=1)[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12044734HCID 12044734, compound

Product 1

HCID 10142908HCID 10142908, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-{Benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amino}-3-(9H-carbazol-4-yloxy)-propan-2-ol (0.18 g, 0.3 mmol) in methanol (6 ml) was added ammonium formate (0.29 g, 4.5 mmol), and 0.045 g 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 isopropyl ether to give 0.14 g of a white solid; m.p. 81-84° C.; MS (ES) m/z 524.0 (MH+); HRMS (ES) Calcd. for C28H34N3O5S (MH+): 524.2219, Found: 524.2252.

Workup

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

Sources & evidence

ORD record
ord-70ebf342f3a342058bf85e9950fc860a
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

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