Sodium hydride → HCID 57675165, compound

HRID 490917Notes

Reaction equation

HRID 490917 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH2:9][C:10]1[N:14]=[C:13]([C:15]2[C:16]([NH:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[C:17]3[CH:23]=[N:22][N:21]([CH2:24][CH3:25])[C:18]3=[N:19][CH:20]=2)[O:12][N:11]=1)=[O:7].[H-].[Na+]>CN(C)C=O.O>[CH2:24]([N:21]1[C:18]2=[N:19][CH:20]=[C:15]([C:13]3[O:12][N:11]=[C:10]([CH2:9][N:8]4[CH2:2][CH2:3][CH2:4][CH2:5][C:6]4=[O:7])[N:14]=3)[C:16]([NH:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[C:17]2[CH:23]=[N:22]1)[CH3:25]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 57675182HCID 57675182, compound

Product 1

HCID 57675165HCID 57675165, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 120 (46 mg, 0.1 mmol) in dry dimethylformamide (2 ml) was added to sodium hydride (60% dispersion in mineral oil, 4.4 mg, 0.11 mmol), and the resulting mixture was stirred at room temperature. After 16 h, the reaction mixture was diluted with water (2 ml) and extracted with chloroform (3×5 ml). The combined organic extracts were dried over anhydrous sodium sulphate and evaporated to give the crude product. Purification of the crude product on a SPE cartridge (silica, 2 g) using a gradient of ethyl acetate in petroleum ether afforded Example 174. LCMS showed MH+=426, TRET=2.66 min.

Workup

  1. extractionextracted with chloroform (3×5 ml)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-b1005866eb4b410b87a366074ed0eae6
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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