Toluene → HCID 178435021, compound

HRID 1772362Notes

Reaction equation

HRID 1772362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:10]=3[NH:11][C:12](=O)[C@@:13]3([CH2:16][C@H:15]3[CH3:17])[N:14]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[NH2:53][NH2:54]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:10]=3[NH:11][C:12](=[N:53][NH2:54])[C@@:13]3([CH2:16][C@H:15]3[CH3:17])[N:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 9321HydrazineHCID 87949Lawesson's reagentHCID 136338068(1S,2R)-5'-(4-chlorophenyl)-2,6',7'-trimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

Product 1

HCID 178435021HCID 178435021, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A round bottomed flask was charged with (1S,2R)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one (289 mg, 0.838 mmol) and a stir bar. Toluene (8.5 mL, 0.1 M) added, followed by Lawesson's Reagent (186 mg, 0.461 mmol), and the reaction was stirred at 110° C. After conversion to the thioamide intermediate, as determined by LC/MS, the reaction was cooled and diluted with THF (20 mL) for the addition of hydrazine (263 μl, 8.38 mmol). The reaction was stirred at room temperature before being concentrated and purified by column chromatography to give (1S,2R)-5′-(4-chlorophenyl)-2′-hydrazono-2,6′,7′-trimethyl-1′,2′-dihydrospiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepine] (249 mg). LRMS (M+H)+: 359 m/z

Workup

  1. temperaturethe reaction was cooled
  2. stirringThe reaction was stirred at room temperature
  3. concentrationbefore being concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-d792863bd3c2438288de8c0ae79a35a2
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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