Triethylamine → 1-(4-(5-Amino-2-(1-(4-fluorophenyl)ethyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl)-2-(4-chlorophenoxy)ethanone

HRID 718242Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[S:11][C:12]3[N:13]=[C:14]([NH2:23])[N:15]=[C:16](S(C)(=O)=O)[C:17]=3[N:18]=2)[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:47]=[CH:46][C:35]([O:36][CH2:37][C:38]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[O:39])=[CH:34][CH:33]=1>O1CCOCC1>[NH2:23][C:14]1[N:15]=[C:16]([N:43]2[CH2:44][CH2:45][N:40]([C:38](=[O:39])[CH2:37][O:36][C:35]3[CH:46]=[CH:47][C:32]([Cl:31])=[CH:33][CH:34]=3)[CH2:41][CH2:42]2)[C:17]2[N:18]=[C:10]([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH3:9])[S:11][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(1-(4-fluorophenyl)ethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine (50 mg, 0.14 mmol) and triethylamine (30 μl, 0.21 mmol) in dioxane (1 ml) was added 2-(4-chlorophenoxy)-1-(piperazin-1-yl)ethanone (51 mg, 0.21 mmol). The reaction mixture was heated at 70° C. for 3 hours. After cooling down to room temperature, the volatiles were removed under reduced pressure. The crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 70:1) furnishing the title compound as a white solid (50 mg, 67%).

Workup

temperatureAfter cooling down to room temperature
customthe volatiles were removed under reduced pressure
customThe crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 70:1)

Sources & evidence

ORD record: ord-11c90d6b81134fb4be8f9d3ded54a380
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193741B2

Reaction notes

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