Triethylamine → 2-(4-Chlorophenoxy)-1-(4-(2-(4-fluorophenyl)-5-methylthiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl)ethanone

HRID 718234Notes

Reaction equation

HRID 718234 reaction equation
Cl[C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:42]=[CH:41][C:30]([O:31][CH2:32][C:33]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[O:34])=[CH:29][CH:28]=1>O1CCOCC1>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]([N:35]2[CH2:40][CH2:39][N:38]([C:2]3[C:3]4[N:11]=[C:10]([C:12]5[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=5)[S:9][C:4]=4[N:5]=[C:6]([CH3:8])[N:7]=3)[CH2:37][CH2:36]2)=[O:34])=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10747602-(4-Chlorophenoxy)-1-(piperazin-1-yl)ethan-1-oneHCID 866624397-Chloro-2-(4-fluorophenyl)-5-methylthiazolo[5,4-d]pyrimidine

Product 1

HCID 469164782-(4-Chlorophenoxy)-1-(4-(2-(4-fluorophenyl)-5-methylthiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl)ethanoneYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7-chloro-2-(4-fluorophenyl)-5-methylthiazolo[5,4-d]pyrimidine (30 mg, 0.11 mmol) and triethylamine (22 μl, 0.16 mmol) in dioxane (1 ml) was added 2-(4-chlorophenoxy)-1-(piperazin-1-yl)ethanone (38 mg, 0.16 mmol). The reaction mixture was heated at 70° C. for 3 hours. After cooling, the volatiles were removed under reduced pressure. The crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 70:1) to yield the title compound as a white solid (40 mg, 75%).

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed under reduced pressure
  3. customThe crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 70:1)

Sources & evidence

ORD record
ord-dcddfdca619d46f38aa6bfcbbcc1fc4e
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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