Diethyl Ether → HCID 59464110, compound

HRID 1713805Notes

Reaction equation

HRID 1713805 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[O:13][C:12]([C:14]([NH:16][C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:22]=3)=[O:15])=[N:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37].[CH3:40][CH2:41][O:42][CH2:43]C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:43][O:42][CH2:41][CH2:40][Si:36]([CH3:38])([CH3:37])[CH3:35])[C:9]2[O:13][C:12]([C:14]([N:16]([C:17]3[CH:18]=[N:19][C:20]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:21][CH:22]=3)[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[O:15])=[N:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 68683733HCID 68683733, compound

Product 1

HCID 59464110HCID 59464110, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-[(3-Iodophenyl)amino]-N-(6-morpholin-4-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide (Example 146) (610 mg, 1.24 mmol) was added portionwise to an ice-cooled suspension of sodium hydride (60% dispersion in oil) (119 mg, 2.97 mmol) in anhydrous DMF (5 mL) in dry glassware. The mixture was stirred at 0° C. for 10 minutes and ambient temperature for 30 minutes then recooled in an ice bath and [2-(chloromethoxy)ethyl](trimethyl)silane (0.482 mL, 2.73 mmol) was added dropwise. The mixture was allowed to warm up and stirred for 16 h. ether (60 mL) was added, and the mixture was washed with water (3×20 mL) and the aqueous extracts were re-extracted with ether (20 mL). The organic extracts were combined, dried and concentrated by evaporation and the residue was purified by chromatography, eluting with 0-20% ether/DCM to give the title compound (610 mg, 65%) as gum; 1H NMR δ 8.09 (1H, s), 7.94 (1H, s), 7.74 (1H, d), 7.59-7.40 (2H, m), 7.28 (1H, t), 6.86 (1H, d), 5.24-5.11 (1H, m), 3.80-3.48 (12H, m), 0.98-0.84 (4H, m), 0.10-0.05 (18H, m).

Workup

  1. temperaturecooled
  2. customthen recooled in an ice bath
  3. temperatureto warm up
  4. additionwas added
  5. washthe mixture was washed with water (3×20 mL)
  6. extractionthe aqueous extracts were re-extracted with ether (20 mL)
  7. customdried
  8. concentrationconcentrated by evaporation
  9. customthe residue was purified by chromatography
  10. washeluting with 0-20% ether/DCM

Sources & evidence

ORD record
ord-a30d0ad21f2d4eb295b75c58bb3a0560
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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