(2S)-2-(3-Methoxypropyl)piperazine → (S)-7-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131448Notes

Reaction equation

HRID 131448 reaction equation
Cl.[F:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([NH2:15])=[N:14][C:5]=2[CH:4]=1.[CH3:19][O:20][CH2:21][CH2:22][CH2:23][C@H:24]1[CH2:29]N[CH2:27][CH2:26][NH:25]1>C1(C)C=CC=CC=1.CS(C)=O>[F:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([N:15]3[CH2:27][CH2:26][NH:25][C@@H:24]([CH2:23][CH2:22][CH2:21][O:20][CH3:19])[CH2:29]3)=[N:14][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 45099475(2S)-2-(3-Methoxypropyl)piperazineHCID 1361924197-Fluoro-2-methyl-10H-thieno(2,3-b)(1,5)benzodiazepin-4-amine monohydrochloride

Product 1

HCID 136090382(S)-7-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azuleneYield 86.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Combine 7-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (270 mg, 0.95 mmol), (S)-2-(3-methoxy-propyl)-piperazine (330 mg, 2 mmol) in a mixture of toluene and dimethylsulfoxide (1:2) and stir at 110° C. for 24 hours. Evaporate the mixture then purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 5% 2N ammonia-methanol in dichloromethane gives (S)-7-fluoro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (320 mg, 0.82 mmol): mass spectrum (APCI): m/z=389.1 (M+1).

Workup

  1. customEvaporate the mixture
  2. customthen purify by flash chromatography
  3. washeluting with a step gradient

Sources & evidence

ORD record
ord-f1d1abc1fb1e4e19a4f04631101bdd3d
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

Loading…