2-Chloro-N,N-dimethylethylamine → 5-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine

HRID 1482933ノート

反応式

HRID 1482933 の反応式
[CH2:1]([O:3][C:4]1[CH:32]=[C:31]([F:33])[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]([OH:30])=[CH:19][N:18]=3)=[N:10]2)=[C:6]([F:34])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:42][CH2:43][N:44]([CH3:46])[CH3:45]>CN(C=O)C>[CH3:45][N:44]([CH3:46])[CH2:43][CH2:42][O:30][C:20]1[C:21]([NH:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)=[N:22][C:17]([C:11]2[C:12]3[CH2:16][CH2:15][CH2:14][C:13]=3[N:9]([CH2:8][C:7]3[C:6]([F:34])=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:32][C:31]=3[F:33])[N:10]=2)=[N:18][CH:19]=1

参加物

5

反応物 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 1362464902-[1-(4-Ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta-[c]pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol

生成物 1

HCID 722026965-[2-(dimethylamino)ethoxy]-2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4H-cyclopenta[c]pyrazol-3-yl]-N-pyridin-4-ylpyrimidin-4-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]-pyrazol-3-yl]-4-(pyridin-4-ylamino)pyrimidin-5-ol 2-2-1 (0.215 mmol, 1.00 eq.) were dissolved in 8 mL of dry DMF and 149 mg potassium carbonate (1.08 mmol, 5.00 eq.) and 47 mg 2-chloro-N,N-dimethylethanamine (0.323 mmol, 1.50 eq.) were added. The reaction mixture was stirred over night at 50° C. The reaction mixture was partitioned between aqueous half saturated sodium chloride solution and DCM/isopropanol (4:1). The separated aqueous layer was extracted 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 51 mg (0.09 mmol, 42%) of analytically pure target compound.

後処理

  1. customThe reaction mixture was partitioned between aqueous half saturated sodium chloride solution and DCM/isopropanol (4:1)
  2. extractionThe separated aqueous layer was extracted 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 51 mg (0.09 mmol, 42%) of analytically pure target compound

出典と根拠

ORDレコード
ord-4719120e5b4944e1a1d92b1bff29b8ea
出典データセット
uspto-grants-2016_08
特許番号
US09416125B2

反応ノート

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