Hydrochloric Acid → HCID 11684859, compound

HRID 2244023Notes

Reaction equation

HRID 2244023 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23](C#N)=[CH:22][CH:21]=3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].[N-]=[N+]=[N-].[Na+].[Cl-].C([NH+](CC)CC)C.Cl.[NH:47]1[CH:51]=[N:50][N:49]=[N:48]1>C1(C)C=CC=CC=1.C(OCC)C.C(OCC)(=O)C>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[C:24]([C:51]4[N:47]=[N:48][NH:49][N:50]=4)[CH:25]=3)(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 59212579HCID 59212579, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 11684859HCID 11684859, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-N-(4-cyano-phenyl)-benzenesulfonamide (1.44 g, 3.10 mmol), sodium azide (2.02 g, 31.0 mmol) and triethyl ammonium chloride (4.27 g, 31.0 mmol) in toluene (10.3 mL) and heat to reflux for 2 hours. Cool to ambient temperature and add 1N hydrochloric acid (20 mL) and ethyl acetate (20 mL). Extract the aqueous phase with ethyl acetate (2×20 mL), dry (sodium sulfate) and condense under reduced pressure. Sonicate resulting red residue in diethyl ether for 1 hour, collect the title compound by filtration as a white solid (831 mg, 1.64 mmol): 1H NMR (DMSO-d6) δ 0.82 (t, 3H), 1.45 (m, 2H), 2.57 (m, 5H), 5.30 (s, 2H), 6.62 (d, 1H), 7.30 (m, 1H), 7.45 (t, 1H), 7.60 (m, 2H), 7.67 (m, 2H), 7.78 (d, 1H), 7.85 (m, 3H), 10.65 (s, 1H), 12.82 (s, 1H) tetrazole H not observed; MS (m/z): 506 (M−1). The following compounds are prepared essentially by the method of Example 8.

Workup

  1. temperatureto reflux for 2 hours
  2. extractionExtract the aqueous phase with ethyl acetate (2×20 mL)
  3. customdry
  4. custom(sodium sulfate) and condense under reduced pressure
  5. customSonicate
  6. customcollect the title compound
  7. customThe following compounds are prepared essentially by the method of Example 8

Sources & evidence

ORD record
ord-0898adbe4555461180bf3bb3c01e06a1
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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