HCID 67429406, compound → HCID 67261828, compound

HRID 1040199Notes

Reaction equation

HRID 1040199 reaction equation
[CH3:1][C:2]1([CH3:35])[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[C:17]([NH:19][C:20]4[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=4)[CH:16]=[C:15]([CH3:30])[CH:14]=3)=[CH:11][N:12]=2)[CH2:5][CH2:4][CH:3]1[C:31]([O:33][CH3:34])=[O:32].[H][H]>[Pd].CO>[CH3:1][C:2]1([CH3:35])[CH2:7][CH:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[C:17]([NH:19][C:20]4[N:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][N:21]=4)[CH:16]=[C:15]([CH3:30])[CH:14]=3)=[CH:11][N:12]=2)[CH2:5][CH2:4][CH:3]1[C:31]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 2

HCID 67429406HCID 67429406, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 67261828HCID 67261828, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 887MethanolSolvent4×

Procedure

10% Palladium on carbon (30 mg, 0.028 mmol) was taken up in methanol (1 mL) under argon. A solution of the product from Step 1 (141 mg, 0.281 mmol) in methanol (3 mL) was then added. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen. The mixture was allowed to stir over the weekend. The reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was taken up in methanol (3 mL) and added to a flask containing 10% Palladium on carbon (30 mg, 0.028 mmol) in 1 mL methanol. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen and stirred for 24 hours. The reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was taken up in methanol (3 mL) and added to a flask containing 10% Palladium on carbon (30 mg, 0.028 mmol) in 1 mL methanol. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen and stirred for one week. The mixture was then filtered through a plug of celite and the celite was washed methanol. The filtrate was concentrated under reduced pressure to afford methyl 2,2-dimethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylate (87 mg, 0.17 mmol, 62% yield) as a light yellow oily solid. MS ESI: [M+H]+ m/z 505.1.

Workup

  1. customthe flask was evacuated
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. additionadded to a flask
  5. customthe flask was evacuated
  6. stirringstirred for 24 hours
  7. filtrationThe reaction was filtered through celite and
  8. concentrationconcentrated under reduced pressure
  9. additionadded to a flask
  10. customthe flask was evacuated
  11. stirringstirred for one week
  12. filtrationThe mixture was then filtered through a plug of celite
  13. washthe celite was washed methanol
  14. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe58478df54d40989594c7f108ca48c7
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

Loading…