Trifluoroacetic acid → HCID 71157223, compound

HRID 536955Notes

Reaction equation

HRID 536955 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3(O)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[NH:24][C:25]([C:28]#[N:29])=[CH:26][N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:30][S:31]([O-:33])=[O:32].[Na+].C(O)(C(F)(F)F)=O>CO>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:20][C:21]([C:23]2[NH:24][C:25]([C:28]#[N:29])=[CH:26][N:27]=2)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2733271Sodium methanesulfinateHCID 24874733HCID 24874733, compound

Product 1

HCID 71157223HCID 71157223, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(4-hydroxy-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in Example 27, 75 mg, 0.19 mmol) and sodium methylsulfinate (195 mg, 1.90 mmol) in 4 mL of methanol was added 0.28 mL (3.80 mmol) of TFA. The mixture was stirred overnight at 70° C. and then concentrated in vacuo. The crude residue was partitioned in EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was dried (Na2SO4) and then concentrated in vacuo. The residue was purified by preparative TLC on silica gel (20% ethyl acetate-hexane) to afford the title compound as a light brown oil (18 mg, 21%). 1H-NMR (CDCl3; 400 MHz): δ 9.64 (s, 1H), 8.32 (d, 1H, J=8.0), 7.71 (s, 1H), 7.33 (m, 1H), 7.23 (d, 1H, J=1.8 Hz), 5.87 (s, 1H), 3.90-3.81 (m, 4H), 3.01 (s, 3H), 2.30-2.25 (m, 4H), 2.07-1.79 (m, 8H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was partitioned in EtOAc (20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC on silica gel (20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3bacc02155ca4ee7a43e57111ac13930
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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