Dimethylformamide → N-(Benzylsulfonyl)-7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanamide

HRID 517900Notes

Reaction equation

HRID 517900 reaction equation
[C:1]1([CH3:33])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=O)[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[C:54]1([CH2:60][S:61]([NH2:64])(=[O:63])=[O:62])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.CCCC(C)C>C(Cl)Cl.CCOC(C)=O.O>[CH2:60]([S:61]([NH:64][C:30](=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:20]1[C:10]2=[N:11][C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:33])=[CH:6][CH:5]=3)[N:8]=[C:9]2[CH2:23][CH2:22][CH2:21]1)(=[O:63])=[O:62])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

10

Reactant 6

HCID 6228DimethylformamideHCID 78922-MethylpentaneHCID 65578Oxalyl chlorideHCID 78318BenzenemethanesulfonamideHCID 81531DiisopropylethylamineHCID 566444827,8-Dihydro-2,3-bis(4-methylphenyl)pyrido[2,3-b]pyrazine-5(6H)-heptanoic acid

Product 1

HCID 71656342N-(Benzylsulfonyl)-7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid [prepared according to the preparation procedures disclosed in PCT patent application PCT/EP2011/062028, Example 4.3] (100 mg, 0.225 mmol) in dry DCM (5 ml) at RT, under nitrogen, was treated with DMF (1.746 μl, 0.023 mmol) followed by oxalyl chloride (0.022 ml, 0.248 mmol). After stirring at RT for 2 hours, DIPEA (0.157 ml, 0.902 mmol) was added followed by phenylmethane sulfonamide (154 mg, 0.902 mmol). The resulting mixture was stirred at RT for 2 hours and subsequently added to water (30 ml). The mixture was extracted with DCM (×3) and the combined organic extracts were passed through a phase separating column. The organic solvent was removed under reduced pressure and purification of the crude residue by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded an orange solid. The solid was dissolved in a minimal volume of EtOAc and treated with an excess of iso-hexane. The resulting suspension was filtered and the solid rinsed with iso-hexane (×3) the afford the titled compound;

Workup

  1. customprepared
  2. customaccording to the preparation procedures
  3. customat RT
  4. stirringThe resulting mixture was stirred at RT for 2 hours
  5. extractionThe mixture was extracted with DCM (×3)
  6. customseparating column
  7. customThe organic solvent was removed under reduced pressure and purification of the crude residue by chromatography on silica eluting with 0-40% EtOAc in iso-hexane
  8. customafforded an orange solid
  9. filtrationThe resulting suspension was filtered
  10. washthe solid rinsed with iso-hexane (×3) the

Sources & evidence

ORD record
ord-e54e96880f624859bd979a0b6cfb3d73
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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