Diisopropylethylamine → (R)-4-[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-(2,2,2-trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279159ノート

反応式

HRID 2279159 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([C:27](O)=[O:28])[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=2)=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][NH:49][C@H:48]([CH2:52][C:53]([F:56])([F:55])[F:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>C(Cl)Cl.O>[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:27]([C:13]2[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=3)[CH:12]=2)=[O:28])[C@H:48]([CH2:52][C:53]([F:55])([F:56])[F:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 72210106(R)-3-(2,2,2-Trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

生成物 1

HCID 90013556(R)-4-[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-(2,2,2-trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 0.80 g of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 12 ml of DCM were added 1 ml of Hünig's base, 0.48 g of BEP and 0.50 g of (R)-3-(2,2,2-trifluoroethyl)-piperazine-1-carboxylic acid tert-butyl ester. The reaction was stirred at r.t. for 2 d. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 0.58 g (60%) of the title compound.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

出典と根拠

ORDレコード
ord-88ee32782b944209b60c3720f6321a5d
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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