Toluene → HCID 136005564, compound

HRID 1350428Notes

Reaction equation

HRID 1350428 reaction equation
[C:1]1([CH2:11][CH2:12][C@H:13]2[CH2:18][NH:17][CH2:16][CH2:15][NH:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=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.C1(C)C=CC=CC=1.C(N(C(C)C)C(C)C)C>C(OCC)(=O)C.O.C(O)(=O)C.CS(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:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH2:18]3)[C:22]=2[CH:21]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 58860672HCID 58860672, compoundHCID 135446208Olanzamine

Product 1

HCID 136005564HCID 136005564, compoundYield 5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

Combine (S)-2-(2-naphthalen-1-yl-ethyl)-piperazine (686 mg, 2.85 mmol), 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (654 mg, 2.85 mmol), toluene (5.7 mL), DMSO (1.4 mL) and glacial acetic acid (0.5 mL). Add N-ethyldiisopropylamine (2.0 mL). Heat at 105° C. After 48 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 (0.5%–5%) as the eluent to give 183 mg. Purify again by radial silica gel chromatography using a 2 mm plate and 2N ammonia in methanol-methylene chloride (1%–2%) as the eluent to give 60 mg (5%) of the title compound: mass spectrum (ion spray): m/z=453 (M+1), 451 (M−1). Analysis calculated for C28H28N4S.0.2H2O: C, 73.71; H, 6.27; N, 12.28. Found: C, 73.37; H, 6.19; N, 12.00.

Workup

  1. temperaturecool to ambient temperature
  2. extractionExtract with ethyl acetate
  3. washWash the extracts with water and brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by silica gel chromatography
  8. customto give 183 mg
  9. customPurify again by radial silica gel chromatography

Sources & evidence

ORD record
ord-cfca0f2850d64d90851acc099a161228
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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