Iodine → HCID 86658564, compound

HRID 1520212Notes

Reaction equation

HRID 1520212 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[N:3]=1.II.[F:14][C:15]([F:34])([F:33])[CH2:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH:23]=1)=O>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:22]2[CH:23]=[C:19]([C:17]3[N:11]=[C:9]([NH:8][C:4]4[N:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=4)[S:10][C:16]=3[C:15]([F:34])([F:14])[F:33])[CH:20]=[N:21]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 807IodineHCID 13607523HCID 13607523, compoundHCID 67433884HCID 67433884, compound

Product 1

HCID 86658564HCID 86658564, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 9 Step 3: To a solution of 1-(4-methylpyrimidin-2-yl)thiourea (0.79 mmol, 133 mg) in pyridine (1 mL) was added iodine (0.79 mmol, 200 mg). The solution was stirred at 80° C. for 15 minutes and then 3,3,3-trifluoro-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (0.79 mmol, 235 mg) was added. The reaction mixture was stirred for 2 hours at 80° C. The solvent was removed under reduced pressure. The crude mixture was partitioned between AcOEt and a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with AcOEt. The combined organic layers were dried over MgSO4, were filtered and were evaporated under reduced pressure. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (99:1) to afford 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)-5-(trifluoromethyl)thiazol-2-amine (0.40 mmol, 180 mg, 51%).

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at 80° C
  2. customThe solvent was removed under reduced pressure
  3. customThe crude mixture was partitioned between AcOEt
  4. extractionThe aqueous layer was extracted with AcOEt
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationwere filtered
  7. customwere evaporated under reduced pressure
  8. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-23198a975a104404a16208f2ac45f00b
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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