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Thiophenol → 2-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol

HRID 1482932
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HRID 1482932 반응식
[CH2:1]([O:3][C:4]1[CH:33]=[C:32]([F:34])[C:7]([CH2:8][N:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[C:11]([C:17]3[N:22]=[C:21]([NH:23][C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[C:20]([O:30]C)=[CH:19][N:18]=3)=[N:10]2)=[C:6]([F:35])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>CN1CCCC1=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([F:35])[C:7]([CH2:8][N:9]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[C:11]([C:17]3[N:22]=[C:21]([NH:23][C:24]4[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=4)[C:20]([OH:30])=[CH:19][N:18]=3)=[N:10]2)=[C:32]([F:34])[CH:33]=1)[CH3:2]
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참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 722022542-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine

생성물 1

HCID 1362464902-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
150 °C

실험 절차

461 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine 2-1-1 (0.964 mmol, 1.00 eq.) were dissolved in 42 mL of dry 1-methylpyrrolidin-2-one. 51 mg of potassium carbonate (0.366 mmol, 0.38 eq.) and 150 μL benzenethiol (1.45 mmol, 1.5 eq.) were added. The mixture was stirred for 1 h at 150° C. bath temperature. The reaction mixture was partitioned between aqueous half saturated ammonium chloride solution and DCM/isopropanol (4:1). The separated aqueous layer was extracted twice with DCM/isopropanol (4:1). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The purification of the residue by flash chromatography provided 349 mg (0.75 mmol, 78%) of analytically pure target compound.

후처리

  1. customThe reaction mixture was partitioned between aqueous half saturated ammonium chloride solution and DCM/isopropanol (4:1)
  2. extractionThe separated aqueous layer was extracted twice with DCM/isopropanol (4:1)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe purification of the residue by flash chromatography
  6. customprovided 349 mg (0.75 mmol, 78%) of analytically pure target compound

출처 및 근거

ORD 기록
ord-f5a65d3cc91f4c648489ab6523846554
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09416125B2

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