Hydrochloric Acid → HCID 67273692, compound

HRID 598224Notes

Reaction equation

HRID 598224 reaction equation
CO[C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].C(N([CH2:17][CH3:18])CC)C.C([CH:21]([C:25](Cl)=[O:26])[C:22](Cl)=[O:23])C.[O-:28]CC.[Na+].Cl>ClCCl.O>[OH:4][C:3]1[C:5]2[N:6]=[CH:7][CH:8]=[N:9][C:10]=2[NH:11][C:25](=[O:26])[C:21]=1[C:22]([O:23][CH2:17][CH3:18])=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 2723922Sodium ethoxideHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 67273692HCID 67273692, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-aminopyrazine-2-carboxylic acid methyl ester (0.596 g, 3.89 mmol) in dichloromethane (20.0 mL) was treated with triethylamine (2.65 mL, 19.40 mmol) followed by ethyl malonyl chloride (2.44 mL, 19.40 mmol). The mixture was stirred at ambient temperature overnight. The solution was concentrated in vacuo and the residue was dissolved in ethanol (15.0 mL). The solution was treated with sodium ethoxide (7.20 mL, 19.40 mmol, 21% solution in ethanol) at ambient temperature and stirred for 2 h. The solution was dissolved with water and treated with 6N aqueous hydrochloric acid. The solid formed was filtered and washed with diethyl ether to afford the title compound as a yellow solid (0.667 g, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.3 (s, 1H), 8.68 (d, J=2.3 Hz, 1H), 8.57 (d, J=2.3 Hz, 1H), 4.26 (q, J=7.2 Hz, 2H), 1.27 (t, J=7.1 Hz, 3H). MS(ES+) m/e 235 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethanol (15.0 mL)
  3. stirringstirred for 2 h
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1009b47704a64dbf9e885b2ad367e7e3
Source dataset
uspto-grants-2011_03
Patent number
US07897612B2

Reaction notes

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