Ethanol → (2-Fluoro-4-iodo-phenyl)-{4-[5-(2-morpholin-4-yl-ethylamino)-[1,3,4]oxadiazol-2-yl]-pyridin-3-yl}-amine

HRID 658371Notes

Reaction equation

HRID 658371 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=[O:13].C(Cl)Cl.IC.[CH2:25]([OH:27])[CH3:26]>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]1[O:13][C:17]([NH:18][CH2:19][CH2:10][N:9]2[CH2:3][CH2:2][O:27][CH2:25][CH2:26]2)=[N:15][N:14]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 6344DichloromethaneHCID 115888023-[(2-Fluoro-4-iodophenyl)amino]isonicotinohydrazide

Product 1

HCID 59026835(2-Fluoro-4-iodo-phenyl)-{4-[5-(2-morpholin-4-yl-ethylamino)-[1,3,4]oxadiazol-2-yl]-pyridin-3-yl}-amine

Procedure

To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (500 mg; 1.34 mmol; 1 eq) in DCM (5 mL) 4-(3-Isothiocyanato-ethyll)-morpholine (255 mg; 1.61 mmol; 1.2 eq) was added. The reaction mixture was refluxed for 4 hrs under argon. A yellow solid precipitated out, which was filtered to afford an intermediate that was suspended in ethanol (5 mL). Iodomethane (190 mg; 1.34 mmol; 1.0 eq) was then added and the reaction mixture was stirred overnight at RT. It was then heated to 80° C. and stirred for another 2 hr. Filtration afforded the yellow solid product 153 mg. LC/MS (Method A) [0.41 min; 511(M+1)]

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hrs under argon
  2. customA yellow solid precipitated out
  3. filtrationwhich was filtered
  4. customto afford an intermediate
  5. temperatureIt was then heated to 80° C.
  6. stirringstirred for another 2 hr
  7. filtrationFiltration

Sources & evidence

ORD record
ord-30c4e096ff874bae9bc0a8e3207b5068
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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