Dimethyl Sulfoxide → HCID 135797726, compound

HRID 1350418Notes

Reaction equation

HRID 1350418 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][C:23]([CH2:26][CH2:27][C@H:28]2[CH2:33]N[CH2:31][CH2:30][NH:29]2)=[CH:22][CH:21]=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:21]=[CH:22][C:23]([CH2:26][CH2:27][C@@H:28]2[NH:29][CH2:30][CH2:31][N:17]([C:6]3[C:5]4[CH:4]=[C:3]([CH3:2])[S:12][C:11]=4[NH:10][C:9]4[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=4[N:7]=3)[CH2:33]2)=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 51970802HCID 51970802, compoundHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135797726HCID 135797726, compoundYield 42%

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-(4-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 380.3 mg (42%) of the title compound as a brown foam: mp 78°, 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-8daf8639156142b383e02b60019fd914
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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