Ammonium formate → HCID 86614438, compound

HRID 1038079Notes

Reaction equation

HRID 1038079 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH:21][C:22]([C:24]4([CH:36]([OH:38])[CH3:37])[CH2:28][CH2:27][N:26](CC5C=CC=CC=5)[CH2:25]4)=[O:23])[CH:19]=3)[N:14]([C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:13]=2)=[CH:8][CH:7]=1>CO.[Pd]>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH:21][C:22]([C:24]4([CH:36]([OH:38])[CH3:37])[CH2:28][CH2:27][NH:26][CH2:25]4)=[O:23])[CH:19]=3)[N:14]([C:39]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67418578HCID 67418578, compound

Product 1

HCID 86614438HCID 86614438, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Added ammonium formate (100 mg, 1.58 mmol) to a suspension of 1-Benzyl-3-(1-hydroxy-ethyl)-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1-trityl-indazol-5-yl]-amide (5N) (80 mg, 0.114 mmol) and 10% Pd/C (5 mg) in MeOH (5 ml) at room temperature then refluxed for 4 hours. The reaction was cooled, diluted with MeOH (20 ml) and filtered through a celite pad. The filtrate was concentrated and the residue dissolved in MeCl2 (40 ml), dried over MgSO4, filtered and solvent evaporated yielding 6N as a solid (60 mg, 87%) ESMS (MH, 611).

Workup

  1. temperaturethen refluxed for 4 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through a celite pad
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue dissolved in MeCl2 (40 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvent evaporated

Sources & evidence

ORD record
ord-223911cbda6d4450b2420e833bf057b3
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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