Cesium carbonate → [2-(2,6-Dichloro-4-methanesulfonylphenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(2,6-dimethylpyrimidin-4-yl)amine

HRID 626686노트

반응식

HRID 626686 반응식
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:12]=3[Cl:22])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[N:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:17][C:16]1[CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=[C:12]([Cl:22])[C:11]=1[N:9]1[CH:8]=[C:7]2[C:2]([NH:23][C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[N:25]=3)=[N:3][CH:4]=[CH:5][C:6]2=[N:10]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970454-Chloro-2-(2,6-dichloro-4-methanesulfonylphenyl)-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 69671279[2-(2,6-Dichloro-4-methanesulfonylphenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-(2,6-dimethylpyrimidin-4-yl)amine수율 59.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

A suspension of 4-chloro-2-(2,6-dichloro-4-methanesulfonylphenyl)-2H-pyrazolo[4,3-c]pyridine (75 mg, 0.20 mmol), 4-amino-2,6-dimethylpyrimidine (27 mg, 0.22 mmol), Pd2(dba)3 (5 mg, 0.005 mmol), Xantphos (12 mg, 0.02 mmol) and cesium carbonate (130 mg, 0.40 mmol) in dioxane (2 mL) was sealed in a microwave vial, purged with nitrogen, and irradiated at 150° C. for 30 minutes in the microwave. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-1% methanol in ethyl acetate) to afford the title compound as a yellow solid (55 mg, 59% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.60 (br s, 1H), 9.21 (s, 1H), 8.32 (s, 2H), 8.30 (s, 1H), 7.99 (d, J=6.4 Hz, 1H), 7.21 (d, J=6.4 Hz, 1H), 3.48 (s, 3H), 2.49 (s, 3H), 2.40 (s, 3H). LCMS (Method B): RT=2.80 min, m/z: 463 [M+H+].

후처리

  1. customwas sealed in a microwave vial
  2. custompurged with nitrogen
  3. customirradiated at 150° C. for 30 minutes in the microwave
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (0-1% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-5ab35d177b434488a1a8f3077fc02bd1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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