Dimethylformamide → HCID 68233580, compound

HRID 1429373Notes

Reaction equation

HRID 1429373 reaction equation
N1[C:10]2[C:5](=[C:6]([S:11]([N:14]3[CH2:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[CH2:18][O:17][CH2:16][C@H:15]3[CH2:26][OH:27])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=CC=1.[H-].[Na+].[CH3:30]I.C[N:33]([CH:35]=O)[CH3:34]>>[CH3:30][O:27][CH2:26][C@H:15]1[N:14]([S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:34]=2[N:33]=[CH:35][CH:4]=[CH:5]3)(=[O:13])=[O:12])[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[CH2:18][O:17][CH2:16]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71269376HCID 71269376, compound

Product 1

HCID 68233580HCID 68233580, compoundYield 53%

Procedure

To a solution of compound 15 (40 mg, 0.1 mmol) in DMF (3 mL) at 0° C. was added NaH (168 mg, 0.4 mmol). The mixture was stirred at rt for 0.5 h and to it was added MeI (22 mg, 0.16 mmol). The reaction was stirred at rt for 2.5 h, quenched with H2O and extracted with EA (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give compound 16 (22 mg, 53% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 8.51 (d, 1H, J=8.0 Hz), 8.16 (d, 1H, J=8.0 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.60 (t, 1H, J=8.0 Hz), 7.46-7.43 (m, 1H), 7.18 (d, 1H, J=8.0 Hz), 7.00 (d, 1H, J=7.6 Hz), 6.91-6.82 (m, 2H), 5.12 (d, 1H, J=8.0 Hz), 4.99-4.90 (m, 2H), 4.72 (s, 1H), 4.62-4.59 (d, 1H), 4.23 (d, 1H, J=8.0 Hz), 3.76 (d, 1H, J=8.8 Hz), 3.60 (t, 1H, J=8.0 Hz), 3.33-3.29 (m, 1H), 3.17 (s, 3H). MS (ESI) calcd for [C21H22N2O4S+H]+ (m/z): 399.48. found: 399.2.

Workup

  1. stirringThe reaction was stirred at rt for 2.5 h
  2. customquenched with H2O
  3. extractionextracted with EA (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by Prep-TLC

Sources & evidence

ORD record
ord-8389b07d61ba47db96d1eabe400fc7dd
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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