Triethylamine → HCID 11269508, compound

HRID 736388Notes

Reaction equation

HRID 736388 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[NH:20][CH:21]=[CH:22][N:23]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl.O.Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:20]([S:33]([CH3:32])(=[O:35])=[O:34])[CH:21]=[CH:22][N:23]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11232415HCID 11232415, compound

Product 1

HCID 11269508HCID 11269508, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 6 (71.4 mg, 0.224 mmol) and triethylamine (62 μL, 0.44 mmol) in CH2Cl2 (2 mL) at 0° C. were treated with methanesulfonyl chloride (21 μL, 0.27 mmol). The solution was stirred for 40 minutes, allowed to warm over 15 minutes, diluted with water (3 mL) and 1 N HCl (0.5 mL), and extracted with CH2Cl2 (3×4 mL). The extracts were combined, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (60% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 7.96 (d, 2H), 7.85 (m, 3H), 7.57 (m, 3H), 7.41 (d, 2H), 7.22 (d, 1H), 3.02 (s, 3H), 1.33 (s, 9H); MS (m/z) 398.

Workup

  1. temperatureto warm over 15 minutes
  2. extractionextracted with CH2Cl2 (3×4 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e897ab59c12242f18de1c86f7305e220
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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