Dimethylformamide → HCID 68865405, compound

HRID 494155Notes

Reaction equation

HRID 494155 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([S:24]([OH:27])(=O)=[O:25])=[N:7]1.[CH3:32][N:33](C=O)[CH3:34].S(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([S:24]([N:33]([CH3:34])[CH3:32])(=[O:25])=[O:27])=[N:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86624803HCID 86624803, compound

Product 1

HCID 68865405HCID 68865405, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-4-sulfonic acid (32 mg, 68 μmol), anhydrous DMF (11 μL, 0.14 mmol), and thionyl chloride (1.05 g, 8.84 mmol) in anhydrous acetonitrile (0.6 mL) was heated at 80° C. for 30 minutes. The resultant mixture was concentrated under vacuum. The residue was dissolved in anhydrous acetonitrile (3 mL) and treated with a solution of dimethylamine in THF (1 mL, 2 M). The mixture was stirred at room temperature for one hour and treated with aqueous sodium hydroxide (0.5 mL, 1 M). After stirring at room temperature for one hour, the product mixture was concentrated under vacuum. The residue was subjected to reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in anhydrous acetonitrile (3 mL)
  3. additiontreated with a solution of dimethylamine in THF (1 mL, 2 M)
  4. additiontreated with aqueous sodium hydroxide (0.5 mL, 1 M)
  5. stirringAfter stirring at room temperature for one hour
  6. concentrationthe product mixture was concentrated under vacuum
  7. customphase preparative HPLC purification
  8. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-83f6792fe5e545189300d85c6974cdc6
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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