Potassium Carbonate → 4-{2-Methoxy-4-[3-(2-morpholin-4-yl-ethyl)-2,4-dioxo-thiazolidin-5-ylidenemethyl]-phenoxy}-3-trifluoromethyl-benzonitrile

HRID 574066Notes

Reaction equation

HRID 574066 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:27]=[CH:26][C:12]([O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=3[C:22]([F:25])([F:24])[F:23])=[C:11]([O:28][CH3:29])[CH:10]=2)[S:3]1.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+].[Al]>CN(C=O)C>[CH3:29][O:28][C:11]1[CH:10]=[C:9]([CH:8]=[C:4]2[S:3][C:2](=[O:1])[N:6]([CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:5]2=[O:7])[CH:27]=[CH:26][C:12]=1[O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[C:22]([F:23])([F:24])[F:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 5359268AluminumHCID 752532344-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-2-methoxy-phenoxy]-3-trifluoromethyl-benzonitrile

Product 1

HCID 725771084-{2-Methoxy-4-[3-(2-morpholin-4-yl-ethyl)-2,4-dioxo-thiazolidin-5-ylidenemethyl]-phenoxy}-3-trifluoromethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-2-methoxy-phenoxy]-3-trifluoromethyl-benzonitrile (40 mg, 0.095 mmol) and 4-(2-Chloro-ethyl)-morpholine (0.095 mmol) in DMF (1.5 mL) was treated with K2CO3 (33 mg, 0.24 mmol) and heated to 80° C. in an aluminum heating block. After 12 h, the reaction was cooled to RT and partitioned between EtOAc (5 mL) and H2O (5 mL). The organic phase was washed with H2O (2×5 mL), dried over Na2SO4 and concentrated in vacuo. Silica gel chromatography (MeOH/CH2Cl2) afforded the title compound. 1H NMR (400 Hz, CDCl3) δ 7.97 (d, 1H), 7.87 (s, 1H), 7.68 (dd, 1H), 7.19 (m, 3H), 6.76 (d, 1H), 3.90 (t, 2H), 3.82 (s, 3H), 3.67 (bs, 4H), 2.64 (t, 2H), 2.51 (bs, 4H); LC/MS (m/z) [M+1]+ 534.2 (calculated for C25H23F3N3O5S, 534.12).

Workup

  1. custompartitioned between EtOAc (5 mL) and H2O (5 mL)
  2. washThe organic phase was washed with H2O (2×5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be96d0a1a8b641e193002ee568a5da49
Source dataset
uspto-grants-2015_05
Patent number
US09034852B2

Reaction notes

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