Dimethylformamide → HCID 9930603, compound

HRID 1815444Notes

Reaction equation

HRID 1815444 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:31]=[CH:30][C:7]([CH2:8][N:9]([CH2:21][CH2:22][CH2:23][CH2:24]N2CCCC2)[C:10]([NH:12]CC2C=CC(Cl)=CC=2)=[NH:11])=[CH:6][CH:5]=1.[H-].[Na+].Br[CH2:35][CH2:36][CH2:37][CH2:38]CBr.[CH3:41][N:42](C=O)C>>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:41][N:42]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:10]([NH2:12])=[NH:11])=[CH:30][CH:31]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 178478773HCID 178478773, compound

Product 1

HCID 9930603HCID 9930603, compound

Procedure

To an ice-cooled stirred solution of the product from Example 52 step a (725 mg, 3.00 mmol) in DMF (9 ml) was added, in a single portion, sodium hydride (60% dispersion in mineral oil, 144 mg, 3.60 mmol). The coolant was removed and the suspension was stirred at ambient temperature for 30 minutes. The suspension was cooled in ice and 1,5-dibromopentane (1.23 ml, 9.03 mmol) was added in three portions. The coolant was removed and the reaction mixture was stirred at ambient temperature for 18 h. The reaction was quenched with water (40 ml) and then extracted with ethyl acetate (40 ml). The aqueous phase was discarded and the organic phase washed twice with brine (40 ml). The organic phase was dried over anhydrous magnesium sulfate and the filtrate evaporated at reduced pressure. The residue was purified by flash column chromatography (5:1 hexane:ethyl acetate) to afford the title product.

Workup

  1. customThe coolant was removed
  2. temperatureThe suspension was cooled in ice
  3. customThe coolant was removed
  4. stirringthe reaction mixture was stirred at ambient temperature for 18 h
  5. customThe reaction was quenched with water (40 ml)
  6. extractionextracted with ethyl acetate (40 ml)
  7. washthe organic phase washed twice with brine (40 ml)
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. customthe filtrate evaporated at reduced pressure
  10. customThe residue was purified by flash column chromatography (5:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-5a03463d75ec4be4af19e1febc29aac6
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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