1,2-Diaminocyclohexane → HCID 11996714, 화합물

HRID 655861노트

반응식

HRID 655861 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(N)CCCCC1N.[NH:21]1[C:25]2=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]2[CH:23]=[N:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu](I)I.C(OCC)(=O)C>[N:11]1[NH:12][C:8]([C:4]2[CH:3]=[C:2]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]4[CH:23]=[N:22]3)[CH:7]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1

참가 물질

8

반응물 4

HCID 46101,2-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 27356133-(3-Bromophenyl)-1H-pyrazole

생성물 1

HCID 11996714HCID 11996714, 화합물수율 0.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

5-(3-bromo-phenyl)-1H-pyrazole (0.3 g, 1.0 eq, 1.34 mmol) and cyclohexane-1,2-diamine (0.03 g, 0.2 eq, 0.27 mmol) were added to a pre-stirred mixture of 1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine (0.22 g, 1.2 eq, 1.62 mmol), copper iodide (0.013 g, 0.5 eq, 0.68 mmol) and potassium phosphate (0.6 g, 2.1 eq, 2.84 mmol) in DMF (8 ml) under an inert atmosphere. The reaction mixture was then stirred at 110° C. for 24 hours, and allowed to cool to room temperature. Ethyl acetate (8 ml) was then added to the reaction mixture which was then filtered through a plug of silica, which was then washed with a further portion of ethylacetate (20 ml). The filtrate was concentrated to dryness in vacuo and the resultant residue was purified by column chromatography using DCM/MeOH (95:5) as eluent to yield the title compound as an off-white solid (0.9 mg, 0.0003 mmol, 0.2%). LCMS: [M+H]+=277, Rt=1.80 min, 93% purity.

후처리

  1. temperatureto cool to room temperature
  2. filtrationwas then filtered through a plug of silica, which
  3. washwas then washed with a further portion of ethylacetate (20 ml)
  4. concentrationThe filtrate was concentrated to dryness in vacuo
  5. customthe resultant residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-185a36f64512478fb6b8733d88e86fcd
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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