Morpholine → 5-Morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047153노트

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HRID 2047153 반응식
Cl[C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.C(N(CC)C(C)C)(C)C.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>CN1C(=O)CCC1>[O:50]1[CH2:51][CH2:52][N:47]([C:2]2[CH:7]=[C:6]([NH2:8])[N:5]3[N:25]=[CH:26][C:27]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:4]3[N:3]=2)[CH2:48][CH2:49]1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

생성물 1

HCID 581733995-Morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
200 °C

실험 절차

To a 2-5 mL microwave vessel is charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (72 μmol, 40 mg), N,N-diisopropylethylamine (220 μmol, 38 μL), NMP (2 mL), and morpholine (220 μmol, 19 μL). The reaction vessel is flushed with agron and sealed. The reaction mixture was heated to 200° C. in microwave synthesizer for 30 minutes. Upon completion, the NMP was removed in vacuo as an azeotropic using chlorobenzene. The crude product was purified via reverse-phase preparatory HPLC to yield 5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as brown-yellow solid. (m+H=347.31, retention time=2.97 min).

후처리

  1. customThe reaction vessel is flushed with agron
  2. customsealed
  3. customUpon completion, the NMP was removed in vacuo as
  4. customThe crude product was purified via reverse-phase preparatory HPLC

출처 및 근거

ORD 기록
ord-f55c7f7e8d7244e5a87269a85b1ef299
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591943B2

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