Dimethyl Sulfoxide → HCID 58592783、化合物

HRID 642881ノート

反応式

HRID 642881 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 58592783HCID 58592783、化合物収率 93%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cfb92ad8568f43219a4062cc457e24dd
出典データセット
uspto-grants-2010_04
特許番号
US07696210B2

反応ノート

読み込み中…