2-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thione → (S)-10-[3-(2-phenylsulfanyl-ethyl)piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diazabenzo[f]azulene

HRID 131481Notes

Reaction equation

HRID 131481 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5](=S)[C:4]=2[CH:3]=1.[C:17]1([S:23][CH2:24][CH2:25][C@H:26]2[CH2:31][NH:30][CH2:29][CH2:28][NH:27]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:17]1([S:23][CH2:24][CH2:25][C@@H:26]2[NH:27][CH2:28][CH2:29][N:30]([C:5]3[C:4]4[CH:3]=[C:2]([CH3:1])[S:11][C:10]=4[NH:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[N:6]=3)[CH2:31]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 210935012-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thioneHCID 58625875(S)-2-(2-phenylsulfanyl-ethyl)-piperazine

Product 1

HCID 136090413(S)-10-[3-(2-phenylsulfanyl-ethyl)piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diazabenzo[f]azuleneYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione (0.455 g, 1.85 mmol), (S)-2-(2-phenylsulfanyl-ethyl)-piperazine (0.411, 1.85 mmol) and pyridine (5 mL) and reflux for 36 hours. Evaporate the mixture and apply the material to 10 g of SCX, then elute with methanol followed by 5% 2N ammonia-methanol in dichloromethane and then 2N ammonia-methanol. Purification by flash chromatography, eluting with a step gradient starting with dichloromethane going to 7% 2N ammonia-methanol in dichloromethane gives (S)-10-[3-(2-phenylsulfanyl-ethyl)-piperazin-1-yl]-2-methyl 4H-3-thia-4,9-diazabenzo[f]azulene (0.126 g, 0.290 mmol, 16%). Mass spectrum (APCI): m/z=435.1 (M+1).

Workup

  1. customEvaporate the mixture
  2. washapply the material to 10 g of SCX, then elute with methanol
  3. customPurification by flash chromatography
  4. washeluting with a step gradient

Sources & evidence

ORD record
ord-de21a0853e05415a8216d7169a3c657c
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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