Iodine → 3-[5-(2-Methyl-1H-imidazol-1-yl)-2-(2-pyrazinylamino)-1,3-thiazol-4-yl]benzonitrile

HRID 2214766Notes

Reaction equation

HRID 2214766 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=O)[CH:4]=[CH:5][N:6]=1.[N:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[NH:24][C:25]([NH2:27])=[S:26].II.N1C=CC=CC=1>O>[CH3:1][C:2]1[N:3]([C:7]2[S:26][C:25]([NH:24][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][N:18]=3)=[N:27][C:8]=2[C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 1049PyridineHCID 2771013N-PyrazinylthioureaHCID 21948404HCID 21948404, compound

Product 1

HCID 102919483-[5-(2-Methyl-1H-imidazol-1-yl)-2-(2-pyrazinylamino)-1,3-thiazol-4-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(2-Methylimidazol-1-yl-acetyl)-benzonitrile (13.8 g, 0.06 mol) is mixed with pyrazinyl-2-thiourea (9.4 g, 0.06 mol), iodine (15.6 g, 0.06 mol) and pyridine (60 ml). The mixture is stirred, initially at room temperature and then at 60° C. overnight (17.5 hours). The mixture obtained is allowed to cool to room temperature and water (50 ml) added. The solid obtained is filtered off, stirred in water (50 ml) for 30 minutes, and filtered off again. The resulting solid is dried at 40° C. in vacuo over P2O5 to give the title compound.

Workup

  1. customat 60° C.
  2. customovernight (17.5 hours)
  3. customThe mixture obtained
  4. temperatureto cool to room temperature
  5. customThe solid obtained
  6. filtrationis filtered off
  7. stirringstirred in water (50 ml) for 30 minutes
  8. filtrationfiltered off again
  9. dry with materialThe resulting solid is dried at 40° C. in vacuo over P2O5

Sources & evidence

ORD record
ord-17dd3010644f45378a24ef7adaa44eb5
Source dataset
uspto-grants-2006_09
Patent number
US07109202B2

Reaction notes

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