1,8-Diazabicyclo(5.4.0)undec-7-ene → (2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-N-(5-chloro-2-methoxyphenyl)acetamide

HRID 448025ノート

反応式

HRID 448025 の反応式
[I-].[CH2:2]([N+:6]1[N:10]=[C:9]([CH3:11])[S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].C1CCN2C(=NCCC2)CC1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([O:34][CH3:35])=[C:29]([N:31]=[C:32]=[O:33])[CH:30]=1>O>[CH2:2]([N:6]1[N:10]=[C:9]([CH3:11])[S:8]/[C:7]/1=[CH:12]\[C:32]([NH:31][C:29]1[CH:30]=[C:25]([Cl:24])[CH:26]=[CH:27][C:28]=1[O:34][CH3:35])=[O:33])[CH2:3][CH2:4][CH3:5]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1440094-Chloro-2-isocyanato-1-methoxybenzeneHCID 691879173-Butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide

生成物 1

HCID 24955351(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-N-(5-chloro-2-methoxyphenyl)acetamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of the product from Example 47A (149 mg, 0.5 mmol), DBU (105 μL, 0.75 mmol) and 5-chloro-2-methoxy phenyl isocyanate (91 mg, 0.5 mmol) was stirred overnight. The solution was diluted with water (10 mL), extracted with dichloromethane (3×5 mL). The organic layers were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo. The residue was purified by the HPLC procedure specified in Example 47B to obtain the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.5 Hz, 3 H), 1.27-1.39 (m, 2 H), 1.64-1.75 (m, 2 H), 2.36 (s, 3 H), 3.82-3.91 (m, 5 H), 5.81 (s, 1 H), 6.92-7.01 (m, 2 H), 8.36 (d, J=2.4 Hz, 1 H), 8.68 (s, 1 H); MS (ESI) m/z 354 (M+H)+. Anal. Calcd for C16H20ClN3O2S.0.5 C2HF3O2: C, 48.92; H, 4.92; N, 9.99. Found: C, 49.28; H, 5.09; N, 10.07.

後処理

  1. extractionextracted with dichloromethane (3×5 mL)
  2. washwashed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by the HPLC procedure

出典と根拠

ORDレコード
ord-b4d26e3ad980402c851c0a08c885cfd6
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

反応ノート

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