Methanol → HCID 59703815, compound

HRID 908616Notes

Reaction equation

HRID 908616 reaction equation
[F:1][CH:2]([F:47])[O:3][C:4]1[CH:46]=[CH:45][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:18]3[S:19][C:20]4[C:25](Cl)=[N:24][C:23]([C:27]([F:30])([F:29])[F:28])=[N:22][C:21]=4[N:31]=3)[CH2:15][CH2:14][N:13]2[S:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)(=[O:34])=[O:33])=[O:11])=[CH:6][CH:5]=1.C([O-])=O.[NH4+].CO>C(O)C.[C].[Pd]>[F:47][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:18]3[S:19][C:20]4[CH:25]=[N:24][C:23]([C:27]([F:30])([F:29])[F:28])=[N:22][C:21]=4[N:31]=3)[CH2:15][CH2:14][N:13]2[S:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)(=[O:33])=[O:34])=[O:11])=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 59703720HCID 59703720, compound

Product 1

HCID 59703815HCID 59703815, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Under a nitrogen atmosphere, to a solution of the compound (1.09 g) obtained in Step 9 and ammonium formate (895 mg) in ethanol (15 ml)-methanol (5 ml) was added 10% palladium carbon (1.0 g). After stirring at 85° C. for 1 hr, the catalyst was filtered off. The filtrate was concentrated under reduced pressure, and the residue was partitioned by adding ethyl acetate and water. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the title compound (596 mg).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was partitioned
  4. additionby adding ethyl acetate and water
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-4628f08620a7476883ce4815cd663282
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

Loading…