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1,2-Diaminocyclohexane, trans- → HCID 52914387、化合物

HRID 594963
ノート
印刷プレビュー

反応式

HRID 594963 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.CCOC(C)=O.[Cu](I)I>[CH3:29][N:24]([C:21]1[CH:22]=[CH:23][C:18]([N:14]2[C:12]3=[N:13][C:8]([NH:7][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[N:9][CH:10]=[C:11]3[CH:16]=[N:15]2)=[CH:19][CH:20]=1)[S:25]([CH3:28])(=[O:26])=[O:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 56980471HCID 56980471、化合物HCID 66765655N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine

生成物 1

HCID 52914387HCID 52914387、化合物

試薬・触媒・溶媒 3

HCID 83717
Copper iodide
触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

A suspension of N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (see Example 1, step (i)) (60 mg, 0.28 mmol), N-(4-bromophenyl)-N-methylmethanesulfonamide (1.1 eq), copper iodide (0.1 eq), potassium phosphate (2 eq) and trans-1,2-diaminocyclohexane (0.1 eq) in dioxane (2 mL) was heated in the microwave at 160° C. for 2 h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give the title product. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.33 (s, 1H), 8.19 (d, 2H), 7.97 (s, 1H), 7.66 (d, 2H), 7.60 (s, 1H), 3.84 (s, 3H), 3.01 (s, 3H); LC-MS method B, (ES+) 399.1, RT=8.18 min.

後処理

  1. temperatureAfter cooling to rt the mixture
  2. washwashed with water
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography (petroleum ether: EtOAc)

出典と根拠

ORDレコード
ord-38591bbc083542338292cb55b7285a43
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242987B2

反応ノート

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