Sodium hydride → HCID 178485929, compound

HRID 2047485Notes

Reaction equation

HRID 2047485 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([N:13]([CH3:45])[C:14]([N:16]([CH3:44])[C@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]([C@H:31]3[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:43])[CH2:39][CH2:40][CH2:41]Cl)[CH2:33][CH2:32]3)=[O:30])[CH2:18]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+]>CN(C=O)C.O>[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([N:13]([CH3:45])[C:14]([N:16]([C@H:17]2[C@H:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:20][N:19]([C:29]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:41][CH2:40][CH2:39][C:38]4=[O:43])[CH2:33][CH2:32]3)=[O:30])[CH2:18]2)[CH3:44])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 24758Sodium hydride3×HCID 178485931HCID 178485931, compound

Product 1

HCID 178485929HCID 178485929, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (0.2 g) obtained in step 1 in DMF (5.6 mL) was added sodium hydride (0.017 g) at 0° C., and the mixture was stirred at room temperature for 6 hr. To the mixture was added sodium hydride (0.017 g), and the mixture was stirred at room temperature for 12 hr, and sodium hydride (0.017 g) was further added. The mixture was stirred at room temperature for 6 hr, diluted with water and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→10% methanol/ethyl acetate) to give the title compound (0.14 g, 76%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. stirringThe mixture was stirred at room temperature for 6 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 1N hydrochloric acid, water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified by silica gel column chromatography (solvent gradient; 0→10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-f5b20d502ea84e328d46f172e40e9bb4
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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