2-Furancarbonyl chloride → HCID 118079001, compound

HRID 1485737Notes

Reaction equation

HRID 1485737 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][C@H:11]1[CH2:16][NH:15][C:14]2[CH:17]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[N:19]=[CH:20][C:13]=2[N:12]1[C:31](=[O:33])[CH3:32].[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39](Cl)=[O:40]>ClCCl>[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39]([N:15]1[CH2:16][C@H:11]([CH3:10])[N:12]([C:31](=[O:33])[CH3:32])[C:13]2[CH:20]=[N:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=3)=[CH:17][C:14]1=2)=[O:40]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 118079709HCID 118079709, compound

Product 1

HCID 118079001HCID 118079001, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (0.3 mL, 1.718 mmol) was added to a solution of (S)-1-(3-methyl-7-(4-(methylsulfonyl)phenyl)-2,3-dihydropyrido[4,3-b]pyrazin-4(1H)-yl)ethanone (0.004 g, 0.012 mmol) and furan-2-carbonyl chloride (0.2 mL, 2.029 mmol) in dichloromethane (1.0 mL), and the mixture stirred at room temperature for 2 h. The reaction mixture was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a yellow oil. This material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford (S)-1-(1-(furan-2-carbonyl)-3-methyl-7-(4-(methylsulfonyl)phenyl)-2,3-dihydropyrido[3,4-b]pyrazin-4(1H)-yl)ethanone (0.0038 g, 75%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.13-1.22 (m, 3 H), 2.25 (br s, 1 H), 2.31 (s, 3 H), 3.02 (s, 3 H), 3.88 (br s, 1 H), 4.05-4.18 (m, 1 H), 5.03 (br s, 1 H), 6.55 (dd, J=3.52, 1.76 Hz, 1 H), 7.20-7.26 (m, 1 H), 7.45 (dd, J=1.76, 0.88 Hz, 1 H), 7.78 (s, 1 H), 7.89-8.02 (m, 4 H). MS (ESI, pos. ion) m/z 440.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customThe aqueous phase was separated
  3. extractionextracted with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customThis material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-74811aec4fd24f74b839ceab8202581a
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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