Iodoethane → HCID 86292191, compound

HRID 873932Notes

Reaction equation

HRID 873932 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:17]3[C:13](=[N:14][N:15]([CH3:19])[C:16]=3[OH:18])[C:12](=[O:20])[N:11]2[C:21]2[CH:26]=[C:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[CH:22]=2)=[CH:6][CH:5]=1.I[CH2:31][CH3:32]>CN(C=O)C.CCOC(C)=O.O.CCOCC>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:17]3[C:13](=[N:14][N:15]([CH3:19])[C:16]=3[O:18][CH2:31][CH3:32])[C:12](=[O:20])[N:11]2[C:21]2[CH:26]=[C:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[CH:22]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178428083HCID 178428083, compound

Product 1

HCID 86292191HCID 86292191, compoundYield 50.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaH (19.19 mg, 0.48 mmol) was added to a stirred solution of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-hydroxy-2-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6-(2H)-one (Example 73) (142 mg, 0.369 mmol) in DMF (1 mL) at 0° C. and the reaction was stirred at 0° C. for 20 min. Iodoethane (0.036 mL, 0.443 mmol) was added and the resulting mixture was stirred at RT for 20 min. The reaction was diluted with EtOAc and water and both phases separated. The aq. layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (1% ammonia/7.5% MeOH/CH2Cl2) to afford, after trituration in Et2O, the title product (77 mg, 0.186 mmol, 50% yield) as white solid. tR: 0.91 min (LC-MS 2); ESI-MS: 413 [M+H]+ (LC-MS 2); Rf=0.39 (1% ammonia/7.5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=6.8 Hz, 3H) 1.91 (s, 3H) 3.35 (s, 3H) 3.60-3.77 (m, 4H) 3.89-4.03 (m, 1H) 6.20 (s, 1H) 7.25 (d, J=8.6 Hz, 2H) 7.30-7.44 (m, 3H) 7.66 (d, J=2.7 Hz, 1H).

Workup

  1. stirringthe resulting mixture was stirred at RT for 20 min
  2. customboth phases separated
  3. extractionThe aq. layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography (1% ammonia/7.5% MeOH/CH2Cl2)
  7. customto afford

Sources & evidence

ORD record
ord-c357ba196cc243daad5bfe60ddaab209
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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