Water → Methyl 10-bromo-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

HRID 575424Notes

Reaction equation

HRID 575424 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:20]([NH:22][NH:23][C:24]([CH:26]4[CH2:28][CH2:27]4)=O)=O)=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:29]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:20]4[S:39][C:24]([CH:26]5[CH2:28][CH2:27]5)=[N:23][N:22]=4)=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 86693476Methyl 10-bromo-3-(2-(cyclopropanecarbonyl)hydrazinecarbonyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 86693478Methyl 10-bromo-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 10-bromo-3-(2-(cyclopropanecarbonyl)hydrazinecarbonyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was dissolved in toluene (0.56 mL) and treated with Lawesson's reagent (1.3 equiv., 29.8 mg, 0.07359 mmol). The reaction was heated to reflux until judged complete by LC/MS analysis. The solution was cooled to room temperature. Water was added and the solution was extracted 2× with methylene chloride. The organic layers were combined, dried with sodium sulfate and concentrated in vacuo. The crude material was carried forward without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. extractionthe solution was extracted 2× with methylene chloride
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was carried forward without further purification

Sources & evidence

ORD record
ord-7d5c5a013288478c835719c8459b0ec4
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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