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

HRID 658370Notes

Reaction equation

HRID 658370 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].[N:20]([CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[C:21]=S.IC>C(Cl)Cl.C(O)C>[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:21]([NH:20][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[N:15][N:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 27604612-Piperidinoethyl isothiocyanateHCID 11588802HCID 11588802, compound

Product 1

HCID 59026818(2-Fluoro-4-iodo-phenyl)-{4-[5-(2-piperidin-1-yl-ethylamino)-[1,3,4]oxadiazol-2-yl]-pyridin-3-yl}-amineYield 9.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (300 mg; 0.81 mmol; 1 eq) in DCM (5 mL), 1-(2-Isothiocyanato-ethyl)-piperidine (192 mg; 1.13 mmol; 1.4 eq) was added. The reaction mixture was refluxed for 4 hrs under argon. A yellow solid precipitated out and filtered to afford an intermediated that was suspended in ethanol (5 mL). Iodomethane (148 mg; 1.05 mmol; 1.3 eq) was added to the reaction mixture and stirred overnight at RT, then heated to 80° C. and stirred for another 2 hr. The mixture was filtered to give a yellow solid product 40 mg. LC/MS (Method A) [3.89 min; 509(M+1)]

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hrs under argon
  2. customA yellow solid precipitated out
  3. filtrationfiltered
  4. customto afford an intermediated
  5. temperatureheated to 80° C.
  6. stirringstirred for another 2 hr
  7. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-acefdd484b604c318eb206b4e9d40f91
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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