Diisopropylethylamine → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5-trimethyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine

HRID 2279128노트

반응식

HRID 2279128 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27]OS(C)(=O)=O)[CH:12]=2)=[CH:7][CH:6]=1.[CH3:33][CH:34]1[CH2:39][NH:38][C:37]([CH3:41])([CH3:40])[CH2:36][N:35]1[CH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:38]3[CH2:39][CH:34]([CH3:33])[N:35]([CH2:42][C:43]4[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=4)[CH2:36][C:37]3([CH3:40])[CH3:41])[CH:12]=2)=[CH:9][CH:10]=1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 648390912,5,5-Trimethyl-1-(pyridin-3-ylmethyl)piperazineHCID 90014099Methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

생성물 1

HCID 900135336-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5-trimethyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine수율 36.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
140 °C

실험 절차

To a solution of 150 mg of methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester, and 85 mg 2,5,5-trimethyl-1-(pyridin-3-ylmethyl)piperazine in 4 ml of dry THF were added 0.28 ml of DIPEA. The reaction was heated to 140° C. for 60 min in a microwave reactor. The reaction was diluted with ethyl acetate and water and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphaste, filtrated and concentrated. The resulting oil was purified by chromatography (silica, heptanes/ethyl acetate). 69 mg of the title compound were obtained.

후처리

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphaste
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customThe resulting oil was purified by chromatography (silica, heptanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-02090e0ca12b4c9c86680228793a77b8
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133181B2

반응 노트

불러오는 중…