Pyridine → HCID 46916476, compound

HRID 718233Notes

Reaction equation

HRID 718233 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:30][C:31]1[CH:41]=[CH:40][C:34]([O:35][CH2:36][C:37](Cl)=[O:38])=[CH:33][CH:32]=1>CN(C=O)C>[NH2:23][C:12]1[N:13]=[C:14]([N:17]2[CH2:18][CH2:19][N:20]([C:37](=[O:38])[CH2:36][O:35][C:34]3[CH:40]=[CH:41][C:31]([Cl:30])=[CH:32][CH:33]=3)[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

5

Reactant 3

HCID 1049PyridineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 46916336HCID 46916336, compound

Product 1

HCID 46916476HCID 46916476, compoundYield 53.4%

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 (40 mg, 0.12 mmol) and pyridine (15 μl, 0.18 mmol) in DMF (1 ml) was added 4-chlorophenoxyacetyl chloride (27 mg, 0.13 mmol). The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was quenched with water, extracted with EtOAc, brine and was 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 (32 mg, 53%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc, brine
  3. dry with materialwas dried 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-5f05265131db4dc5963cba636fa97c7a
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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