(S)-3-methyl-4-(1-methyl-5-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-yl)morpholine → (S)-4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)aniline

HRID 72189노트

반응식

HRID 72189 반응식
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[C:9]2[N:25]([CH3:26])[N:24]=[CH:23][C:10]=2[N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[N:13]=1>C1COCC1.[Pd]>[CH3:26][N:25]1[C:9]2[C:8]([N:3]3[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]3[CH3:1])=[N:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH:23]=[N:24]1

참가 물질

4

반응물 1

HCID 58222489(S)-3-methyl-4-(1-methyl-5-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-yl)morpholine

생성물 1

HCID 58222503(S)-4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)aniline수율 82.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (S)-3-methyl-4-(1-methyl-5-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-yl)morpholine (122.4 mg, 0.345 mmol) dissolved in anhydrous THF (15 mL) was subjected to a continuous flow hydrogenated apparatus (H-Cube: 10% Pd/C cartridge, 1.0 mL/min flow). The crude was concentrated in vacuo and purified by column chromotagraphy (Si-PPC, gradient 0 to 100% EtOAc in heptane) to give the desired product as a yellow foam (92.0 mg, 82.1%). LC-MS m/z (method A)=325.4 [M+H]+, RT=1.34 min.

후처리

  1. concentrationThe crude was concentrated in vacuo
  2. custompurified by column chromotagraphy (Si-PPC, gradient 0 to 100% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-35dad7700f93441ca23025ec954168e6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828990B2

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