Sodium Hydroxide → 3-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

HRID 1485491ノート

反応式

HRID 1485491 の反応式
[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([NH:17][CH3:18])=[O:16])[C:4]=2[N:5]=[C:6](Cl)[N:7]=1.[OH-].[Na+].[CH2:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32]2[N:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[CH3:25].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>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]>[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([NH:17][CH3:18])=[O:16])[C:4]=2[N:5]=[C:6]([NH:38][C:35]2[CH:36]=[N:37][C:32]([N:29]3[CH2:30][CH2:31][N:26]([CH2:24][CH3:25])[CH2:27][CH2:28]3)=[CH:33][CH:34]=2)[N:7]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866756523-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

生成物 1

HCID 532374933-(4-amino-2-(6-(4-ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide収率 55.2%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide (20 mg, 0.063 mmol) was dissolved in dioxane (1 mL) and then sodium hydroxide (13 mg, 0.31 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (19 mg, 0.094 mmol) were added. After flowing nitrogen gas to the reaction mixture for 10 minutes, Pd2(dba)3 (4 mg, 0.004 mmol) and X-phos (1 mg, 0.12 mmol) were added. The reaction mixture was stirred at 120° C. for 2 hours and filtered with celite. The filtrate was diluted with ethyl acetate and then washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (17 mg, 55% yield) of Example 1.

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. filtrationfiltered with celite
  7. concentrationconcentrated
  8. customPurification by chromatography (5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-3b57ab10dbb84babb69aa893f9454485
出典データセット
uspto-grants-2016_08
特許番号
US09422307B2

反応ノート

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