Dimethyl Sulfoxide → (S)-2-[4-(2-methyl-4H-3-thia-1,4,9-triazabenzo[f]azulene-10-yl)-piperazin-2-yl]-ethanol
Reaction equation
Cl.[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=[C:6]([NH2:17])[C:5]=2[N:4]=1.[NH:18]1[CH2:23][CH2:22]N[CH2:20][C@@H:19]1[CH2:24][CH2:25][OH:26].C(N(C(C)C)CC)(C)C.CS(C)=O>C1(C)C=CC=CC=1>[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=[C:6]([N:17]3[CH2:22][CH2:23][NH:18][C@@H:19]([CH2:24][CH2:25][OH:26])[CH2:20]3)[C:5]=2[N:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Combine 2-methyl-4H-3-thia-1,4,9-triazabenzo[f]azulene-10-ylamine hydrochloride (0.458 g, 1.72 mmol), (S)-2-piperazin-2-yl-ethanol (0.518, 3.98 mmol), diisopropylethylamine (0.346 mL, 1.99 mmol), dimethyl sulfoxide (1.5 mL) and toluene (4.5 mL) and heat to 110° C. for 48 hours. Evaporate the mixture and apply the material to 20 g of SCX, elute with methanol followed by 5% 2N ammonia-methanol in dichloromethane and finally 100% 2N ammonia-methanol. Purify by flash chromatography, eluting with a step gradient starting with dichloromethane going to 10% 2N ammonia-methanol in dichloromethane, to obtain (S)-2-[4-(2-methyl-4H-3-thia-1,4,9-triazabenzo[f]azulene-10-yl)-piperazin-2-yl]-ethanol (0.082 g, 0.239 mmol, 14%): mass spectrum (APCI): m/z=344.4 (M+1).
Workup
- customEvaporate the mixture
- washapply the material to 20 g of SCX, elute with methanol
- customPurify by flash chromatography
- washeluting with a step gradient
Sources & evidence
- ORD record
- ord-985af501d3804760b22f6fdd782e5a9f
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07384934B2
Reaction notes
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