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 448025Notes

Reaction equation

HRID 448025 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b4d26e3ad980402c851c0a08c885cfd6
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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