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4-amino-N-(pyridin-3-ylmethyl)benzamide → 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide

HRID 1011241
ノート
印刷プレビュー

反応式

HRID 1011241 の反応式
Br[C:2]1[C:3]2[N:4]([N:9]=[CH:10][N:11]=2)[C:5]([Cl:8])=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+].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.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:8][C:5]1[N:4]2[N:9]=[CH:10][N:11]=[C:3]2[C:2]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5778334-amino-N-(pyridin-3-ylmethyl)benzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 576643738-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine

生成物 1

HCID 576643524-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide収率 71.8%

試薬・触媒・溶媒 2

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

実験手順

A solution of 8-bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine (100 mg, 0.43 mmol), 4-Amino-N-pyridin-3-ylmethyl-benzamide (108 mg, 0.48 mmol), sodium-tert-butoxide (58 mg, 0.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (39 mg, 40 μmol) and Xantphos (50 mg, 90 μmol) in dioxane is degassed for one minute by nitrogen bubbling and then irradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 30 minutes at 110° C. The solvent is evaporated and the crude is dissolved in dichloromethane and filtered in order to remove the palladium catalyst. The residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5) affording the title compound (117 mg) as a solid.

後処理

  1. customirradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 30 minutes at 110° C
  2. customThe solvent is evaporated
  3. dissolutionthe crude is dissolved in dichloromethane
  4. filtrationfiltered in order
  5. customto remove the palladium catalyst
  6. customThe residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5)

出典と根拠

ORDレコード
ord-59b662cc73ee4a0c8764bd687c820646
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977352B2

反応ノート

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