Dimethyl Sulfoxide → HCID 135797722, compound

HRID 1350419Notes

Reaction equation

HRID 1350419 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.[F:18][C:19]([F:35])([F:34])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][C@H:28]1[CH2:33]N[CH2:31][CH2:30][NH:29]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[F:18][C:19]([F:34])([F:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][C@@H:28]1[NH:29][CH2:30][CH2:31][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)[CH2:33]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 58860694HCID 58860694, compoundHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135797722HCID 135797722, compoundYield 55%

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 (514.5 mg, 1.94 mmol), (S)-2-[2-(2-trifluoromethyl-phenyl)-ethyl]-piperazine (1.00 g, 3.87 mmol), N,N-diisopropylethylamine (250.2 mg, 1.94 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 105° C. After 48 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 497.4 mg (55%) of the title compound as a brown foam: mp 73°, dec; mass spectrum (ion spray): m/z=471.1.

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-2d11d2e7a4f44f9483e4fc4bdbf2a9ed
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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