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Diisopropylethylamine → 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

HRID 550845
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HRID 550845 반응식
FC(F)(F)C(O)=O.[CH3:8][O:9][CH2:10][CH:11]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.C(N(C(C)C)CC)(C)C.C1([O:43][C:44](=O)[NH:45][C:46]2[S:47][C:48]3[N:49]=[CH:50][N:51]=[C:52]([O:55][CH3:56])[C:53]=3[N:54]=2)C=CC=CC=1>C(#N)C>[CH3:56][O:55][C:52]1[C:53]2[N:54]=[C:46]([NH:45][C:44]([N:25]3[CH2:26][CH2:27][N:22]([CH:11]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=4)[CH2:10][O:9][CH3:8])[CH2:23][CH2:24]3)=[O:43])[S:47][C:48]=2[N:49]=[CH:50][N:51]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 59011944(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl esterHCID 866165091-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine trifluoroacetate

생성물 1

HCID 248306114-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide수율 41%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
70 °C

실험 절차

A mixture of 1-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine trifluoroacetate (160 mg, 0.40 mmol) and diisopropylethylamine (0.35 mL, 2.0 mmole) in acetonitrile (10 mL) was heated at 70° C. for ten minutes. After cooling to room temperature, (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester (120 mg, 0.40 mmol) was added to the above solution. The mixture was stirred at reflux for three hours. LCMS analysis indicated complete consumption of starting material. The reaction was concentrated and the crude was purified using reversed phase HPLC to give 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (81 mg, 41% yield) as a white powder. LRMS for C21H23F3N6O3S (M+H)+ at m/z=497. The NMR spectrum obtained on the sample is compatible with its structure.

후처리

  1. temperatureAfter cooling to room temperature
  2. temperatureat reflux for three hours
  3. customconsumption of starting material
  4. concentrationThe reaction was concentrated
  5. customthe crude was purified

출처 및 근거

ORD 기록
ord-bf4f7b464e46492482aac50877825e9d
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947692B2

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