Dichloromethane → HCID 131733692, compound

HRID 705392Notes

Reaction equation

HRID 705392 reaction equation
[CH:1]1([C:4]2[C:5]([N:25]([CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34])[S:26]([CH3:29])(=[O:28])=[O:27])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][CH:21]=[CH:22][N:23]=4)[C:8]=3[CH:24]=2)[CH2:3][CH2:2]1.C(Cl)Cl.C(N(C(C)C)CC)(C)C.[C:48]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])(=[O:51])[NH:49][NH2:50]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([C:4]2[C:5]([N:25]([CH2:30][CH2:31][CH2:32][C:33]([NH:50][NH:49][C:48]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[O:34])[S:26]([CH3:29])(=[O:28])=[O:27])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][CH:21]=[CH:22][N:23]=4)[C:8]=3[CH:24]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 131733693HCID 131733693, compound

Product 1

HCID 131733692HCID 131733692, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

4-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)benzofuran-6-yl)methylsulfonamido)butanoyl chloride (51.9 mg, 0.101 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL) and anhydrous CH2Cl2 (1 mL) under nitrogen. Diisopropylethylamine (0.035 mL, 0.201 mmol) and tert-butyl carbazate (16.28 mg, 0.121 mmol) were added, and the mixture was stirred at 25° C. for 1 hour. Ethyl acetate (50 mL) was added, and the mixture was washed with H2O (3×10 mL) and brine (10 mL), dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation. The crude material was purified by SiO2 flash chromatography (Alltech Extract-Clean™ column, 10 g bed) eluting with 60:40 ethyl acetate/CH2Cl2, followed by 5% methanol/CH2Cl2 to afford the title compound as a white solid (41 mg, 0.067 mmol, 67%). MS (ESI+) m/z 612 (M+H)+, 1223 (2M+H); MS (ESI−) m/z 610 (M−H)−.

Workup

  1. washthe mixture was washed with H2O (3×10 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude material was purified by SiO2 flash chromatography (Alltech Extract-Clean™ column, 10 g bed)
  6. washeluting with 60:40 ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-c3f9cff1bc6e4143a0ec56e1a16be94d
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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