1,2-Dichloroethane → HCID 178513834, compound

HRID 222005

Reaction equation

HRID 222005 reaction equation
[NH:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7]([N:19]=1)=[N:8][C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:10]([OH:12])[N:11]=2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[C:30](O)(=O)[C:31]([NH2:33])=[O:32].C(Cl)CCl.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1.O>[OH:12][C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][C:3]3=[N:1][N:2]=[C:30]([C:31]([NH2:33])=[O:32])[N:19]3[C:7]2=[N:8][C:9]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 974Oxamic AcidHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 178514300HCID 178514300, compound

Product 1

HCID 178513834HCID 178513834, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 6-hydrazinyl-3-phenylpyrido[2,3-b]pyrazin-2(1H)-one (3-3) (300 mg, 1.19 mmol), HOBt (218 mg, 1.42 mmol) and oxamic acid (130 mg, 1.42 mmol) in NMP (12 mL) was added EDC (272 mg, 1.42 mmol) at room temperature and the mixture was stirred for 30 min. After addition of TFA (0.091 mL, 1.19 mmol), the mixture was heated under microwave irradiation at 150° C. for 30 minutes. To a mixture was added water (60 mL) and the precipitate was collected by filtration to give 3-hydroxy-2-phenyl[1,2,4]triazolo[4′,3′:1,6]pyrido[2,3-b]pyrazin-9-carboxamide (9-1) as a yellow powder.

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-66a85126e86f4012a368f42eb2537669
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Linked notes

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