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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
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HRID 1011241 반응식
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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-59b662cc73ee4a0c8764bd687c820646
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977352B2

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