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1,2-Diaminocyclohexane, trans- → HCID 52914387, 화합물

HRID 594963
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HRID 594963 반응식
[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]
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8

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

생성물 1

HCID 52914387HCID 52914387, 화합물

시약·촉매·용매 3

HCID 83717
Copper iodide
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
160 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-38591bbc083542338292cb55b7285a43
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242987B2

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