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

HRID 513279
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HRID 513279 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-45f19abe6290493a8746b619ab6f4dfa
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102625B2

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