Methyl Isocyanate → 2-(3-(2-fluoro-4-iodophenylamino)isonicotinoyl)-N-methylhydrazinecarboxamide

HRID 658390Notes

Reaction equation

HRID 658390 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].[CH3:20][N:21]=[C:22]=[O:23]>CO>[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][NH:15][C:22]([NH:21][CH3:20])=[O:23])=[O:13]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 115888023-[(2-Fluoro-4-iodophenyl)amino]isonicotinohydrazide

Product 1

HCID 590268142-(3-(2-fluoro-4-iodophenylamino)isonicotinoyl)-N-methylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-[(2-fluoro-4-iodophenyl)amino]isonicotinohydrazide (200 mg; 0.54 mmol) in methanol (10 mL) was added (methylimino)(oxo)methane (61 mg; 1.07 mmol) (methyl Isocyanate). After few minutes the reaction mixture became homogeneous, and then an yellow colored solid, 2-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}-N-methylhydrazinecarboxamide (50 mg) was separated out. The filtrate upon concentration gave 158 mg which was also pure. (208 mg, 90%) MS m/z: 429 M+1

Workup

  1. waitAfter few minutes the reaction mixture became homogeneous
  2. customan yellow colored solid, 2-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}-N-methylhydrazinecarboxamide (50 mg) was separated out
  3. concentrationThe filtrate upon concentration
  4. customgave 158 mg which

Sources & evidence

ORD record
ord-dc0c6c8e547247a982ea35d4cafe9041
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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