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 2279128ノート

反応式

HRID 2279128 の反応式
[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

参加物

7

反応物 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

生成物 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]pyridine収率 36.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-02090e0ca12b4c9c86680228793a77b8
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

読み込み中…