Hydrochloric Acid → HCID 24852683, compound

HRID 1818985Notes

Reaction equation

HRID 1818985 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][NH:11][C:10]2[N:15]=[CH:16][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]#N)=[N:23][CH:24]=3)=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([OH:29])[CH3:28].Cl.[O:31]1CCOCC1>>[CH2:27]([O:29][C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:16]=[N:15][C:10]3[NH:11][CH2:12][C:13](=[O:14])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:9]=3[CH:18]=2)=[CH:24][N:23]=1)=[O:31])[CH3:28]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 24852575HCID 24852575, compound

Product 1

HCID 24852683HCID 24852683, compound

Conditions

Temperature
150 °C

Procedure

5-(1-Benzyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)pyridine-2-carbonitrile (32 mg) was mixed with ethanol (1.5 mL) and 4 N HCl (2.0 mL) in dioxane and then heated in a microwave oven at 150° C. for 80 minutes. The reaction mixture was concentrated and purified with preparative reversed-phase HPLC to give the title compound as an orange solid. LCMS: m/z=389.22 (M+H+), 1H-NMR (CD3OD, 400 MHz) δ 1.42 (3H, t, J=7.1 Hz), 4.44 (4H, m), 5.35 (2H, s), 7.28 (1H, m), 7.37 (5H, m), 7.55 (1H, d, J=1.8 Hz), 8.00 (1H, d, J=1.8 Hz), 8.03 (1H, dd, J=8.1, 2.3 Hz), 8.17 (1H, d, J=8.3 Hz), 8.69 (1H, d, J=2.0 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified with preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-83da6ba70c1847dd91282372215f6da0
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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