Diisopropylethylamine → 4-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279122ノート

反応式

HRID 2279122 の反応式
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18]OS(C)(=O)=O)[CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][CH2:33][C:32]1([CH2:41][CH3:42])[CH2:39][CH3:40])=[O:30])([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C>C1COCC1.O>[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([CH2:18][C:4]2[CH:3]=[C:2]([Br:1])[N:7]=[C:6]3[N:8]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][O:13]4)[N:9]=[C:10]([CH3:11])[C:5]=23)[CH2:33][C:32]1([CH2:41][CH3:42])[CH2:39][CH3:40])=[O:30])([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 90013581Methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl esterHCID 900138422,2-Diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 900140904-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester収率 51.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
160 °C

実験手順

A mixture of 500 mg of methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester, 400 mg of 2,2-diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester and 0.43 ml of DIPEA in 8 ml of dry THF was heated to 160° C. for 30 min in a microwave reactor. For workup the mixture was taken up in water and ethyl acetate, the phases were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo and the resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate). 369 mg (50%) of the title compound were obtained.

後処理

  1. customethyl acetate, the phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-6469b407ddd34e8e9df8f259dd0fb3c2
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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