N-methyl-2-pyrrolidone → HCID 136005594, compound

HRID 1350432Notes

Reaction equation

HRID 1350432 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][NH:14]1.[CH3:19][C:20]1[S:29][C:28]2[NH:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]=[C:23](N)[C:22]=2[CH:21]=1.CN1CCCC1=O>C(OCC)(=O)C.O>[CH3:19][C:20]1[S:29][C:28]2[NH:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]=[C:23]([N:17]3[CH2:16][CH2:15][NH:14][C@@H:13]([CH2:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH2:18]3)[C:22]=2[CH:21]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 58860736HCID 58860736, compoundHCID 135446208Olanzamine

Product 1

HCID 136005594HCID 136005594, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine (S)-2-(2-naphthalen-2-yl-ethyl)-piperazine (854 mg, 3.72 mmol), 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (895 mg, 3.72 mmol) and 1-methyl-2-pyrrolidinone (8 mL). Heat at reflux. After 5 h, cool to ambient temperature and dilute with ethyl acetate and 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 576 mg (34%) of the title compound: mass spectrum (ion spray): m/z=453 (M+1), 451 (M−1). HR-MS calculated for C28H29N4S: 453.2113. Found 453.2116. 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 5.7 min; 100% pure.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. extractionExtract with ethyl acetate
  4. washWash the extracts with water and brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate the filtrate
  8. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-8cd8a5b4d339440a84037450a617baf4
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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