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Benzamide → N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

HRID 68658
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HRID 68658 반응식
CNCCNC.I[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:15]=2)[N:10]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:9]=1.[C:39]([NH2:47])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH:26]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:15]=[C:16]3[C:8]([NH:47][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:9][N:10]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:11]3=[N:12][CH:13]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25])([CH3:27])[CH3:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 2331BenzamideHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

생성물 1

HCID 71143663N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide수율 37.4%

시약·촉매·용매

2
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매2회

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온도
95 °C

실험 절차

CuI (95 mg, 0.4988 mmol), and N,N′-dimethylethane-1,2-diamine (176 mg, 1.997 mmol) in dioxane (5 mL) was heated for 5 minutes at 100° C. in a microwave. 1 mL of this solution was added to a mixture of 7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.1720 mmol), benzamide (104.2 mg, 0.8600 mmol) and K3PO4 (73.02 mg, 0.344 mmol) in dioxane (1 mL) and the solution was heated at 95° C. for 1 hour. The reaction mixture is concentrated in vacuo. The residue was partitioned between DCM and water. Combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo yielding an oil which was purified by prep HPLC to give the sub-title product (37 mg, 37%). MS (ES+) 575.1.

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding an oil which
  7. customwas purified by prep HPLC

출처 및 근거

ORD 기록
ord-c9d1960d0ea24e88ab301818a7fa4b81
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822469B2

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