Hydrochloric Acid → HCID 178527543, compound

HRID 1819795Notes

Reaction equation

HRID 1819795 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:26]=3[N:27]=2)[CH:19]=[C:18]([Cl:34])[CH:17]=1)(=[O:14])=[O:13].[N:35]([Si](C)(C)C)=[N+:36]=[N-:37].C([Sn](=O)CCCC)CCC.Cl>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][C:29]([C:32]4[NH:37][N:36]=[N:35][N:33]=4)=[CH:28][C:26]=3[N:27]=2)[CH:19]=[C:18]([Cl:34])[CH:17]=1)(=[O:13])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 18511626HCID 18511626, compound

Product 1

HCID 178527543HCID 178527543, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-Chloro-N-[3-chloro-5-(5-cyano-benzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide (Example 286, 55 mg, 0.1 mmol) in 5 mL of toluene was added azidotrimethylsilane (Aldrich, 26 uL, 0.2 mmol) and dibutyltin oxide (Aldrich, 3 mg, 0.01 mmol). The mixture was heated at 90° C. overnight till there was no starting material remained by TLC. Cooled to room temperature, 1N HCl and EtOAc was added. The mixture was extracted 3× with EtOAc (30 mL). The organic layers were washed twice with a brine solution (300 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography, eluted with 10% EtOAc/CH2Cl2 then 10% MeOH/CH2Cl2 to give 50 mg (85%) of product. 1H NMR (400 MHz, DMSO-d6) δ 8.33 (d, J=8.2 Hz, 1H), 8.30 (d, J=1.6 Hz, 1H), 8.21 (d, J=8.5 Hz, 1H), 8.19 (s, 1H), 8.03 (dd, J=8.4, 1.6 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.44 (t, J=2.0 Hz, 1H), 7.18 (t, J=2.0 Hz, 1H), 7.12 (t, J=1.9 Hz, 1H). MS (EI): m/z 585 (M−H).

Workup

  1. temperatureCooled to room temperature
  2. extractionThe mixture was extracted 3× with EtOAc (30 mL)
  3. washThe organic layers were washed twice with a brine solution (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography
  7. washeluted with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8c61b47ca07b44e797ae8857df76be87
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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