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m-Aminoacetanilide → 6-(3-Acetamidophenylamino)-4-(thiophen-2-ylmethylamino)nicotinamide

HRID 513279
ノート
印刷プレビュー

反応式

HRID 513279 の反応式
Cl[C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[NH:22][C:23](=[O:25])[CH3:24].C1(O[Na])C=CC=CC=1.O.O.O.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]>[C:23]([NH:22][C:21]1[CH:20]=[C:19]([NH:18][C:2]2[CH:10]=[C:9]([NH:11][CH2:12][C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)[CH:28]=[CH:27][CH:26]=1)(=[O:25])[CH3:24]
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 7604m-AminoacetanilideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 584398316-Chloro-4-(thiophen-2-ylmethylamino)nicotinamideHCID 178526975HCID 178526975、化合物

生成物 1

HCID 675018936-(3-Acetamidophenylamino)-4-(thiophen-2-ylmethylamino)nicotinamide収率 12.7%

試薬・触媒・溶媒 2

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

実験手順

A mixture of 6-chloro-4-(thiophen-2-ylmethylamino)nicotinamide (100 mg, 0.373 mmol), 3′-aminoacetanilide (65 mg, 0.433 mmol), PhONa trihydrate (80 mg, 0.471 mmol), xantphos (30 mg, 0.051 mmol) and Pd2 dba3 (20 mg, 0.021 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 3 h. Water and EtOAc were added. The mixture was filtered. The organic phase was separated, washed with aq. 1N NaOH, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give the titled compound (18 mg). MS 382.3 (M+H); UV 251.0 nm; t 0.465 min.

後処理

  1. customwas degassed with Ar
  2. additionWater and EtOAc were added
  3. filtrationThe mixture was filtered
  4. customThe organic phase was separated
  5. washwashed with aq. 1N NaOH
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-45f19abe6290493a8746b619ab6f4dfa
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102625B2

反応ノート

読み込み中…

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