Dimethyl Sulfoxide → HCID 136005563, compound

HRID 1350414Notes

Reaction equation

HRID 1350414 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[CH:4]=1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][C@H:27]1[CH2:32]N[CH2:30][CH2:29][NH:28]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][C@@H:27]1[NH:28][CH2:29][CH2:30][N:17]([C:6]2[C:5]3[CH:4]=[C:3]([CH3:2])[S:12][C:11]=3[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=2)[CH2:32]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 58860679HCID 58860679, compoundHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 136005563HCID 136005563, compoundYield 48.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

Combine 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (607.1 mg, 2.28 mmol), (S)-2-[2-(2-chloro-phenyl)-ethyl]-piperazine (1.03 g, 4.57 mmol), N,N-diisopropylethylamine (295.3 mg, 2.28 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 105° C. After 64 hours, cool the mixture to ambient temperature and then dilute it with ethyl acetate and water. Remove the organic layer and wash it with 1N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using dichloromethane/methanol (95:5) to give 482.4 mg (48%) of the title compound as a brown foam: mp 72°, dec; mass spectrum (ion spray): m/z=437.3.

Workup

  1. temperaturecool the mixture to ambient temperature
  2. customRemove the organic layer
  3. washwash it with 1N NaOH and brine
  4. dry with materialDry (sodium sulfate)
  5. concentrationconcentrate the organic layer to residue
  6. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-30d4565a59f7490d8611e2330bdbeb10
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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