Trifluoroacetic acid → HCID 178491716, compound

HRID 1190210Notes

Reaction equation

HRID 1190210 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14](O)([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[NH:18][C:19]([C:21]2[NH:22][CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[CH:4][CH2:3]1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][SH:38])=[CH:33][CH:32]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:28][C:2]1([CH3:1])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([S:38][CH2:37][C:34]3[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=3)([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=2[NH:18][C:19]([C:21]2[NH:22][CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 804074-Methoxy-alpha-toluenethiolHCID 178424524HCID 178424524, compound

Product 1

HCID 178491716HCID 178491716, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (as prepared in Example 14, step (d), 86 mg, 0.22 mmol) and (4-methoxy-phenyl)-methanethiol (157 μL, 1.13 mmol) in 2 mL of DCM at 0° C. was added 175 μL (2.27 mmol) of TFA. The mixture was allowed to warm to room temperature overnight, at which time it was diluted with DCM (20 mL), washed with water (1×20 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC on silica gel (5% methanol-CHCl3) to afford the title compound (63 mg, 54%). 1H-NMR (CDCl3; 400 MHz): δ 12.78 (br s, 1H), 9.75 (s, 1H), 8.32 (d, 1H, J=8.6 Hz), 7.75 (s, 1H), 7.51 (dd, 1H, J=7.5, 2.1 Hz), 7.41 (d, 1H, J=2.1 Hz), 7.04 (d, 2H, J=8.6 Hz), 6.75 (d, 2H, J=8.6 Hz), 5.80 (m, 1H), 3.75 (s, 3H), 3.41 (s, 2H), 2.31 (m, 2H), 2.13 (m, 2H), 1.72 (s, 6H), 1.61 (t, 2H, J=6.2 Hz), 1.12 (s, 6H).

Workup

  1. washwashed with water (1×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC on silica gel (5% methanol-CHCl3)

Sources & evidence

ORD record
ord-ee7cf66d6128447eb21643cd3f5d086f
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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