Phenyl cyanate → HCID 59026778, compound

HRID 658404Notes

Reaction equation

HRID 658404 reaction equation
C1(O[C:8]#[N:9])C=CC=CC=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[N:25][CH:24]=[C:23]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])[C:18]=1[C:19]([NH:21][NH2:22])=[O:20]>CS(C)=O>[NH2:9][C:8]1[O:20][C:19]([C:18]2[C:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[F:10])=[CH:26][N:25]=[CH:24][C:23]=2[NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[N:21][N:22]=1

Participants

4

Reactant 2

HCID 70740Phenyl cyanateHCID 59026805HCID 59026805, compound

Product 1

HCID 59026778HCID 59026778, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Phenyl cyanate (6 mg, 0.05 mmol) was added to a solution of 3-(2-fluoro-phenyl)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (22 mg, 0.05 mmol) in DMSO (1 mL), and stirred overnight at room temperature. The reaction solution was quenched with H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (15 mg, 65%). LC-MS (M+H=492, obsd.=492). 1H NMR: δ 8.78 (s, 1H), 8.43 (d, 1H), 8.11 (d, 1H), 7.73 (dd, 1H), 7.44 (m, 3H), 7.30 (m, 3H), 7.14 (s, 2H).

Workup

  1. customThe reaction solution was quenched with H2O
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6e53d906c632430f8a117483bef3afc0
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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