Hydrochloric Acid → HCID 69113286, compound

HRID 749023Notes

Reaction equation

HRID 749023 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([NH2:27])[C:22](=[O:26])[N:23]([CH3:25])[CH3:24])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C(N(CC)C(C)C)(C)C.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([C:22](=[O:26])[N:23]([CH3:24])[CH3:25])[NH:27][S:44]([C:41]3[CH:42]=[CH:43][C:38]([CH3:48])=[CH:39][CH:40]=3)(=[O:46])=[O:45])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69113924HCID 69113924, compound

Product 1

HCID 69113286HCID 69113286, compoundYield 48.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

Hydrochloride compound 53 (2.1 g, 5.37 mmol) was dissolved in CH2Cl2 (35 mL) and cooled to 0-5° C. N,N-Diisopropylethylamine (1.87 mL, 11.0 mmol) was added to the above solution followed by addition of p-toluenesulfonyl chloride (0.85 g, 4.46 mmol) in small portions. The reaction mixture was then warmed up to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residual oil was taken up in EtOAc (50 mL). The organic layer was washed with 2.0 M HCl (1×10 mL), saturated NaHCO3 (1×10 mL), and brine (1×25 mL). The resulting EtOAc layer was dried and concentrated under reduced pressure to yield an oil. Flash chromatography (30-50% ethyl acetate in hexane containing 1% acetic acid) yielded the desired sulfonamide 54 (1.1 g, 40%). 1H NMR (DMSO-d6): 8.10 (d, J=9.6 Hz, 1H), 7.55 (d, J=8.0 Hz, 2H), 7.51 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.23 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 4.33 (m, 1H), 3.59 (s, 3H), 2.81-2.90 (m, 3H), 2.75 (s, 3H), 2.62-2.68 (m, 3H), 2.53 (s, 3H), 2.26(s, 3H).

Workup

  1. temperatureThe reaction mixture was then warmed up to room temperature
  2. customThe solvent was removed under reduced pressure
  3. washThe organic layer was washed with 2.0 M HCl (1×10 mL), saturated NaHCO3 (1×10 mL), and brine (1×25 mL)
  4. dry with materialThe resulting EtOAc layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customto yield an oil

Sources & evidence

ORD record
ord-14afeb3ee6be44538f3f1ae1d66f1daf
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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