Phenyl cyanate → HCID 59026802, compound

HRID 658399Notes

Reaction equation

HRID 658399 reaction equation
C1(O[C:8]#[N:9])C=CC=CC=1.[Cl: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[Cl: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 59026773HCID 59026773, compound

Product 1

HCID 59026802HCID 59026802, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Phenyl cyanate (5 mg, 0.04 mmol) was added to a solution of 3-(2-chloro-phenyl)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (7) (17 mg, 0.04 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 (5 mg, 28%). LC-MS (M+H=508, obsd.=508). 1H NMR: δ 8.92 (s, 1H), 8.47 (d, 1H), 8.03 (d, 1H), 7.74 (dd, 1H), 7.55 (m, 2H), 7.43 (m, 3H), 7.24 (t, 1H), 7.11 (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-e9d31e3974aa433eb7aae564aee02b6d
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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