HCID 178418348, compound → HCID 178448418, compound

HRID 1028179Notes

Reaction equation

HRID 1028179 reaction equation
[CH3:1][Li].[CH2:3]([N:7]1[C:11]2[CH2:12][O:13][CH2:14][C:15](=[O:16])[C:10]=2[S:9]/[C:8]/1=[N:17]\[C:18](=[O:28])[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH3:27])[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([N:7]1[C:11]2[CH2:12][O:13][CH2:14][C:15]([OH:16])([CH3:1])[C:10]=2[S:9]/[C:8]/1=[N:17]\[C:18](=[O:28])[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH3:27])[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 178418348HCID 178418348, compoundHCID 178448420HCID 178448420, compound

Product 1

HCID 178448418HCID 178448418, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyllithium (0.8 mL, 1.3 mmol, 1.6M in tetrahydrofuran, Aldrich) in tetrahydrofuran (10 mL) was added slowly a solution of Example 10 (0.25 g, 0.63 mmol) in tetrahydrofuran (5 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes and was allowed to reach room temperature. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-5% methanol in methylene chloride) to afford 92 mg (35%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.3 Hz, 3H), 1.24-1.37 (m, 2H), 1.39 (s, 3H), 1.56-1.76 (m, 2H), 3.64-3.70 (m, J=3.4 Hz, 2H), 3.79 (s, 3H), 3.92-4.13 (m, 2H), 4.55-4.80 (m, 2H), 5.57 (s, 1H), 7.12 (d, J=9.2 Hz, 1H), 7.46 (dd, J=9.0, 2.9 Hz, 1H), 7.73 (s, 1H)); MS (ESI+) m/z 411 (M+H)+.

Workup

  1. customto reach room temperature
  2. customThe reaction mixture was quenched with water (10 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f72a70794b5a4c93a522d2bb828145b8
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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