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Dimethylformamide → HCID 58010001, 화합물

HRID 2204613
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HRID 2204613 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21]O)[N:20]=[C:15]2[CH:14]=1.O=S(Cl)Cl.[N-:36]=[N+:37]=[N-:38].[Na+].CN(C=O)C>C(Cl)Cl>[N:36]([CH2:21][C:19]1[N:20]=[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=1)=[N+:37]=[N-:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 58009987HCID 58009987, 화합물

생성물 1

HCID 58010001HCID 58010001, 화합물수율 89.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (0.63 g, 1.4 mmol) in DCM (10 mL) was treated with SOCl2 (0.115 mL, 1.58 mmol) and stirred for about 15 min at ambient temperature. The solvents were evaporated then sodium azide (0.280 g, 4.31 mmol) and DMF (5 mL) were added. The mixture was then stirred at ambient temperature overnight. The solvent was evaporated and the residue was partitioned between water (30 mL) and EtOAc (25 mL). The aqueous layer was washed with EtOAc (15 mL) then the combined organic solutions were dried over anhydrous MgSO4, filtered, and concentrated to give 2-(azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.58 g, 87%): LC/MS (Table 2, Method a) Rt=3.42 min; MS m/z: 464 (M+H)+.

후처리

  1. customThe solvents were evaporated
  2. stirringThe mixture was then stirred at ambient temperature overnight
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water (30 mL) and EtOAc (25 mL)
  5. washThe aqueous layer was washed with EtOAc (15 mL)
  6. dry with materialthe combined organic solutions were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a426f9903e541a99abf911725348e6d
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365579B2

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