Cesium carbonate → N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 2042212ノート

反応式

HRID 2042212 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH3:29].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>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH:42][C:2]3[N:3]=[CH:4][C:5]4[S:10][CH:9]=[C:8]([C:11]5[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=5)[C:6]=4[N:7]=3)=[CH:38][CH:37]=2)[CH2:34][CH2:35]1)[CH3:29]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 86673215N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

生成物 1

HCID 51347359N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide収率 53.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (20 mg, 0.059 mmol) was dissolved in dioxane (1 mL) and then cesium carbonate (58 mg, 0.18 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (18 mg, 0.088 mmol) were added. After flowing nitrogen gas to the reaction mixture for 10 minutes, Pd(OAc)2 (1 mg, 0.1 mmol) and Xantphos (4 mg, 0.12 mmol) were added. The reaction mixture was stirred at 120° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate and concentrated by filtering with celite. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (16 mg, 53% yield).

後処理

  1. customfor 10 minutes
  2. filtrationfiltered with celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationby filtering with celite
  8. customPurification by chromatography (5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-e0adc1e09bfc4e7f950a9c97ea28c021
出典データセット
uspto-grants-2013_11
特許番号
US08586580B2

反応ノート

読み込み中…