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Sodium Iodide → 1-Benzyl-4-[3-(5-[1,2,4]triazol-4-yl-1H-indol-3-yl)-propyl]-piperazine-2-thione

HRID 609653
ノート
印刷プレビュー

反応式

HRID 609653 の反応式
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH2:15][CH2:16][CH2:17]O)[CH:5]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.S([O-])(=O)(=O)C.[CH2:36]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][C:44]1=[S:49])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>C(O)(C)C.C1COCC1>[CH2:36]([N:43]1[CH2:48][CH2:47][N:46]([CH2:17][CH2:16][CH2:15][C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([N:4]4[CH:3]=[N:2][N:1]=[CH:5]4)[CH:7]=3)[NH:11][CH:10]=2)[CH2:45][C:44]1=[S:49])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 7

HCID 5238Sodium IodideHCID 8471Triethylamine2 回HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2 回HCID 85257MethanesulfonateHCID 106083781-Benzylpiperazine-2-thioneHCID 106339143-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol

生成物 1

HCID 105746711-Benzyl-4-[3-(5-[1,2,4]triazol-4-yl-1H-indol-3-yl)-propyl]-piperazine-2-thione収率 39%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In the same way as that described in Example 2, Step 4, using Intermediate 2 (150 mg, 0.62 mmol), methanesulphonyl chloride (96 μL, 1.24 mmol), triethylamine (172 μL, 1.24 mmol) and THF (80 mL), followed by more triethylamine (86 μL, 0.62 mmol) and methanesulphonyl chloride (48 μL, 0.62 mmol). The resultant crude mesylate was then treated with 1-benzylpiperazine-2-thione (255 mg, 1.24 mmol), K2CO3 (257 mg, 1.9 mmol), sodium iodide (93 mg, 0.62 mmol) and iso-propanol (20 mL). The crude produce was chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (95:5:1), to give the title compound (104 mg) as a pale yellow foam, contaminated with some 1-benzylpiperazin-2-thione. The mixture of thioamides (104 mg) was dissolved in CH2Cl2 (25 mL) and treated with di-tert-butyldicarbonate (50 mg, 0.23 mmol). The mixture was stirred at room temperature for 2 h then the solvent removed in vacuo. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (95:5), to afford the title compound (47 mg, 18%) as a colourless solid, mp. (MeOH) 201-203° C. C24H26N6S. 0.3(H2O) requires: C, 66.12; H, 6.15; N, 19.28%. Found: C, 66.09; H, 5.92; N, 19.23%. 1H NMR (360 MHz, d6 -DMSO) δ1.81-1.92 (2H, m), 2.42 (2H, t, J=7.1 Hz), 2.70-2.76 (4H, m), 3.37-3.42 (2H, m), 3.61 (2H, s), 7.27-7.38 (7H, m), 7.47 (1H, d, J=8.6 Hz), 7.77 (1H, s), 9.01 (2H, s), 11.07 (1H, br s). MS (ES+) (431, M+1).

後処理

  1. customThe crude produce
  2. customwas chromatographed on silica gel
  3. washeluting with CH2Cl2 :MeOH:NH3 (95:5:1)

出典と根拠

ORDレコード
ord-1554a413d96a49fa860f69a0517232e7
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05998415

反応ノート

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