Water → HCID 86624686, compound

HRID 604891Notes

Reaction equation

HRID 604891 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCCCCCC.C([O:16][C:17](=O)[CH2:18][C:19]1[N:20]=[C:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)=[C:27]([O:37][CH3:38])[CH:26]=2)[S:22][CH:23]=1)C.O>O1CCOCC1>[CH3:38][O:37][C:27]1[CH:26]=[C:25]([NH:24][C:21]2[S:22][CH:23]=[C:19]([CH2:18][C:17]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:16])[N:20]=2)[CH:30]=[CH:29][C:28]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 8900HeptaneHCID 86624685HCID 86624685, compound

Product 1

HCID 86624686HCID 86624686, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 80 mg (0.94 mmol) piperidine in dioxane (1 ml) 2M trimethylaluminium solution in heptane (0.94 mmol, 0.47 ml) was carefully added. The solution was stirred at room temperature for 1 hour. A suspension of 100 mg (0.27 mmol) ({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-acetic acid ethyl ester in dioxane (3 ml) was added and the reaction was refluxed over night. Water was added carefully and the reaction was extracted twice with ethyl acetate. The organic layer was dried over sodium sulphate, filtered and the solvent was evaporated under reduced pressure to yield 110 mg (99%) 2-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-1-piperidin-1-yl-ethanone as a brown foam. MS ISP (m/e): 410.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.35 (s, 1H), 7.70 (s, 1H), 7.65 (s, 1H), 7.23 (d, 1H), 7.17 (d, 1H), 7.03 (s, 1H), 6.64 (s, 1H), 3.79 (s, 3H), 3.67 (s, 2H), 3.49 (br t, 2H), 3.42 (br t, 2H), 2.14 (s, 3H), 1.58-1.32 (m, 6H).

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed over night
  3. extractionthe reaction was extracted twice with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e722721842424828b2213bd755d2bb72
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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