4-Methylphenyl isocyanate → HCID 46916428, compound

HRID 718232Notes

Reaction equation

HRID 718232 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[N:11]=[C:12]([NH2:23])[N:13]=[C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[C:24]1([CH3:33])[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>CN(C=O)C>[NH2:23][C:12]1[N:13]=[C:14]([N:17]2[CH2:18][CH2:19][N:20]([C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([CH3:33])=[CH:25][CH:26]=3)=[O:32])[CH2:21][CH2:22]2)[C:15]2[N:16]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[S:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 46916336HCID 46916336, compound

Product 1

HCID 46916428HCID 46916428, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-(4-fluorophenyl)-7-(piperazin-1-yl)thiazolo[5,4-d]pyrimidin-5-amine (50 mg, 0.15 mmol) in DMF (1 ml) was added p-tolyl isocyanate (21 μl, 0.17 mmol) in DMF (0.3 ml). The reaction mixture was stirred for 2 hours at room temperature. The reaction was quenched with water and extracted with EtOAc. The combined organic layers were dried over Na2SO4. After removing the solvents in vacuo, the crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (31 mg, 44%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customAfter removing the solvents in vacuo
  5. customthe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-81585d280f43452d8be532df59aac5f8
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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