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

HRID 131436Notes

Reaction equation

HRID 131436 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.[O:17]([CH2:24][CH2:25][C@H:26]1[CH2:31][NH:30][CH2:29][CH2:28][NH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[O:17]([CH2:24][CH2:25][C@@H:26]1[NH:27][CH2:28][CH2:29][N:30]([C:5]2[C:4]3[CH:3]=[C:2]([CH3:1])[S:11][C:10]=3[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=2)[CH2:31]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 210935012-Methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepine-4-thioneHCID 58626055(S)-2-(2-phenoxyethyl)piperazine

Product 1

HCID 135457500(S)-10-[3-(2-phenoxyethyl)piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diazabenzo[f]azulene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione (0.382 g 1.55 mmol), (S)-2-(2-phenoxyethyl)piperazine (0.320 g, 1.55 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 the title compound: mass spectrum (APCI): m/z=419.1 (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-75ea426153c349d9810acb68e0a01268
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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