Ammonium formate → HCID 15949497, compound

HRID 548701Notes

Reaction equation

HRID 548701 reaction equation
[O:1]=[S:2]1(=[O:33])[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[CH:10][C:5]=2[CH:4]=[CH:3]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[O:33]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[CH:10][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57663196HCID 57663196, compound

Product 1

HCID 15949497HCID 15949497, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-[(1,1-dioxido-1-benzothien-5-yl)oxy]-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (113 mg, 0.24 mmol) in ethanol (2.5 mL) was added ammonium formate (152 mg, 2.40 mmol) and 10% palladium on charcoal (25 mg) and the resultant mixture heated at 140° C. for 10 minutes in a microwave reactor. The catalyst was filtered and the residue reduced, taken up in DCM plus a little methanol and transferred to a silica cartridge, eluted with 0-3% methanol in DCM, to give the desired compound as a clear foam (65 mg).

Workup

  1. filtrationThe catalyst was filtered
  2. washeluted with 0-3% methanol in DCM

Sources & evidence

ORD record
ord-aca44427455b44bdb906e29f43462f6b
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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