Hydrochloric Acid → HCID 66937534, compound

HRID 408783Notes

Reaction equation

HRID 408783 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12](=[NH:14])[NH2:13])[CH:11]=1)=[O:6])[CH3:3].Cl[C:16]1[C:25](Cl)=[N:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>CN(C=O)C.O>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[NH:13][C:16]3=[N:17][C:18]4[C:23]([N:24]=[C:25]3[N:14]=2)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:11]=1)=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 166592,3-DichloroquinoxalineHCID 66937236HCID 66937236, compound

Product 1

HCID 66937534HCID 66937534, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-carbamimidoyl-1H-pyrazole-4-carboxylic acid ethyl ester hydrochloride (0.220 g, 1.00 mmol), 2,3-dichloro-quinoxaline (200 mg, 1.00 mmol), and Cs2CO3 (1.63 g, 5.00 mmol) in DMF (2 mL) was stirred for 4 h. H2O (3 mL) was added and the mixture was acidified to pH 2 with aqueous 1M HCl to form a white precipitate. The precipitate was filtered, triturated with anhydrous EtOH (2 mL), and filtered to yield the titled compound (0.130 g, 43%). MS (CI): mass calcd. for C15H12N6O2, 308.1; m/z found, 309.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 9.08 (s, 1H), 8.23 (s, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.87 (d, J=8.2 Hz, 1H), 7.75 (t, J=7.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

Workup

  1. customto form a white precipitate
  2. filtrationThe precipitate was filtered
  3. customtriturated with anhydrous EtOH (2 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-38a6ab48508844aa82837aad6c0ab250
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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