Dimethyl Sulfoxide → HCID 58592783, 화합물

HRID 642881노트

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HRID 642881 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29](F)[CH:28]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS(C)=O.[N-:41]=[N+:42]=[N-:43].[Na+]>C(OCC)(=O)C>[N:41]([C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[N+:33]([O-:35])=[O:34])[CH2:26][N:23]1[CH2:24][CH2:25][N:20]([C:19]2[C:13]3[N:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)[NH:15][C:14]=3[CH:16]=[CH:17][CH:18]=2)[CH2:21][CH2:22]1)=[N+:42]=[N-:43]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 585927062-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole

생성물 1

HCID 58592783HCID 58592783, 화합물수율 93%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

In a round bottom flask was combined 2-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole (0.197 g, 0.40 mMol), dimethyl sulfoxide (3 mL), and sodium azide (0.029 g, 0.44 mMol) and the mixture stirred overnight. Upon arrival the mixture was diluted with ethyl acetate (100 mL), washed with water (2×50 mL), washed with brine (50 mL), and the organics dried with magnesium sulfate and filtered. The organics were concentrated on a rotary evaporator to yield 190 mg (92% yield) of 4-[4-(3-Azido-4-nitro-benzyl)-piperazin-1-yl]-2-(4-tert-butyl-phenyl)-1H-benzoimidazole as a light yellow solid. 1H NMR (DMSO-d6): δ=12.69 (s, 1H), 8.04 (d, 2H, J=8.7 Hz), 8.01 (d, 1H, J=8.3 Hz), 7.57 (m, 1H), 7.54 (d, 2H, J=8.6 Hz), 7.39 (dd, 1H, J=8.5, 1.2 Hz), 7.03 (m, 2H), 6.50 (dd, 1H, J=5.5, 1.4 Hz), 3.70 (s, 2H), 3.60 (br s, 4H), 2.68 (br s, 4H), 1.33 (s, 9H). LC/MS (Method A), rt=1.41 mins., purity=89.8%, calculated mass=510, [M+H]+=511, [M−H]−=509.

후처리

  1. customIn a round bottom flask was combined
  2. washwashed with water (2×50 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialthe organics dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe organics were concentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-cfb92ad8568f43219a4062cc457e24dd
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696210B2

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