Dimethylformamide → HCID 73855001, compound

HRID 2122004Notes

Reaction equation

HRID 2122004 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([OH:24])[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH3:36])[C:29]#[N:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:38][CH2:39]Br.C([O-])([O-])=O.[K+].[K+].[CH3:47][N:48](C=O)C>>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[C:21]([O:24][CH2:38][CH2:39][NH:48][CH3:47])[CH:22]=[CH:23][C:16]=3[S:15]2)[S:10][C:9]1=[N:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH3:36])[C:29]#[N:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 73855097HCID 73855097, compound

Product 1

HCID 73855001HCID 73855001, compound

Conditions

Temperature
60 °C

Procedure

To the product of Example 57 (62 mg, 0.12 mmol) in anhydrous DMF (2 mL) were added 1,2-dibromoethane (100 mL, 10 equiv) and anhydrous K2CO3 (166 mg, 10 equiv). The suspension was shaken overnight at 60° C. in a sealed tube. After cooling, the reaction mixture was concentrated under reduced pressure, diluted with DCM and acetone, and filtered. The filtrate was concentrated to give a residue, which was purified by chromatography on silica gel, eluting with MeOH-DCM (1:19) to give a yellow solid, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with DCM and acetone
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give a residue, which
  7. customwas purified by chromatography on silica gel
  8. washeluting with MeOH-DCM (1:19)
  9. customto give a yellow solid, which
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-b42675eac6004b53b38f0ed2a92c5de9
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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