Potassium Carbonate → 2-(4-(isoxazol-5-yl)benzyl)-7-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271400노트

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HRID 271400 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N=CN=C(NNC(OC(Cl)(Cl)Cl)=O)C=2C2C=CC=CC=2)=CC=1.Br[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([C:60]2[O:64][N:63]=[CH:62][CH:61]=2)=[CH:56][CH:55]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:64]1[C:60]([C:57]2[CH:58]=[CH:59][C:54]([CH2:53][N:15]3[C:14](=[O:17])[N:11]4[CH:12]=[N:13][C:8]([C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)=[C:9]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:10]4=[N:16]3)=[CH:55][CH:56]=2)=[CH:61][CH:62]=[N:63]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 229975455-(4-(Bromomethyl)phenyl)isoxazoleHCID 58772821Trichloromethyl 2-(6-(4-chlorophenyl)-5-phenylpyrimidin-4-yl)hydrazinecarboxylateHCID 587728227-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

생성물 1

HCID 159536642-(4-(isoxazol-5-yl)benzyl)-7-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

시약·촉매·용매 1

HCID 180Acetone용매

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온도
60 °C

실험 절차

To a stirred solution of 7-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one and/or trichloromethyl 2-(6-(4-chlorophenyl)-5-phenylpyrimidin-4-yl)hydrazinecarboxylate (16.0 mg, 0.05 mmol) in acetone (5 mL) at room temperature under argon was added 5-(4-(bromomethyl)phenyl)isoxazole (23.8 mg, 0.10 mmol), followed by K2CO3 (13.8 mg, 0.10 mmol). The resulting mixture was heated at 60° C. for 17 h. Insoluble material was filtered and rinsed with CH2Cl2. The filtrate was concentrated under reduced pressure and purified by reverse phase preparative HPLC (without TFA). Further purification was performed by silica gel column chromatography eluting with EtOAc-hexanes. Pure product was lyophilized from 1,4-dioxane to obtain the title compound (3.5 mg) as an off-white lyophilate. HPLC/MS: retention time=3.88 min, [M+H]30 =480. 1H NMR (CDCl3): δ 8.71 (s, 1H), 8.28 (d, J=1.2 Hz, 1H), 7.81 (d, J=7.3 Hz, 2H), 7.45 (d, J=7.3 Hz, 2H), 7.26-7.42 (m, 7H), 7.18 (d, J=7.2 Hz, 2H), 6.51(d, J=1.2 Hz, 1H), 5.18 (s, 2H).

후처리

  1. filtrationInsoluble material was filtered
  2. washrinsed with CH2Cl2
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by reverse phase preparative HPLC (without TFA)
  5. customFurther purification
  6. washeluting with EtOAc-hexanes

출처 및 근거

ORD 기록
ord-6868ff5e5a794a9fbb0c02bb755a4d16
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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