Pyridine → HCID 46916426, compound

HRID 1507779Notes

Reaction equation

HRID 1507779 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.N1C=CC=CC=1.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>CN(C=O)C>[CH2:34]([O:33][C:31]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[C:15]3[N:16]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[S:9][C:10]=3[N:11]=[C:12]([NH2:23])[N:13]=2)[CH2:22][CH2:21]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 46916336HCID 46916336, compound

Product 1

HCID 46916426HCID 46916426, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-7-(piperazin-1-yl)thiazolo[5,4-d]pyrimidin-5-amine (50 mg, 0.15 mmol) and pyridine (18 μl, 0.23 mmol) in DMF (1 ml) was added benzyl chloroformate (24 μl, 0.17 mmol). The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was quenched with water, extracted with EtOAc, brine and dried over Na2SO4. After removing the solvents, the crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (54 mg, 77%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc, brine
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvents
  5. customthe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-238b9a5886b8440e853a90e5ba366234
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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