Pyridine → HCID 46916426, compound

HRID 718230Notes

Reaction equation

HRID 718230 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-8b1b8a9a46504c1c836b60b93b25e449
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

Loading…