Dimethyl Sulfoxide → HCID 135932168, compound

HRID 1350436Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C@H:8]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9]2)=[CH:2]1.[CH3:14][C:15]1[S:24][C:23]2[NH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[N:19]=[C:18](N)[C:17]=2[CH:16]=1.C1(C)C=CC=CC=1.CS(C)=O>C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C@@H:8]2[NH:9][CH2:10][CH2:11][N:12]([C:18]3[C:17]4[CH:16]=[C:15]([CH3:14])[S:24][C:23]=4[NH:22][C:21]4[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=4[N:19]=3)[CH2:13]2)=[CH:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

Combine (S)-2-(2-furan-3-yl-ethyl)-piperazine (550 mg, 3.05 mmol), 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (700 mg, 3.05 mmol), toluene (6 mL) and DMSO (1.5 mL). Heat at 100° C. After 48 h, cool to ambient temperature and dilute with ethyl acetate. Filter the solids and dilute the filtrate with water. Extract with ethyl acetate. Wash the extracts with water and brine, dry over sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (2.5%) as the eluent to give 282 mg (24%) of the title compound: mass spectrum (ion spray): m/z=393 (M+1), 391 (M-1). HR-MS calculated for C22H25N4OS: 393.1749. Found 393.1742. HPLC: Symmetry C18 column (3.5 μm, 4.6×50 mm). Gradient 5% to 90% solvent B in 7 min. Solvent A was 0.1% (v/v) TFA in water and solvent B was acetonitrile. Retention time 5.4 min; 100% pure.

Workup

temperaturecool to ambient temperature
filtrationFilter the solids
additiondilute the filtrate with water
extractionExtract with ethyl acetate
washWash the extracts with water and brine
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate the filtrate
customPurify by silica gel chromatography

Sources & evidence

ORD record: ord-068aa6d7732b42789985758e064b9a09
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214673B2

Reaction notes

Loading…