Sodium Methoxide → HCID 86345769, compound

HRID 1772684Notes

Reaction equation

HRID 1772684 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C[O-].[Na+:33]>CO>[Na+:33].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[C:26]([C:28]([O-:30])=[O:29])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86345770HCID 86345770, compound

Product 1

HCID 86345769HCID 86345769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a slurry of (E)-2-(2-(8-morpholinoimidazo[1,2-a]pyrazin-2-yl)vinyl)quinoline-4-carboxylic acid (32 mg, 0.08 mmol) in MeOH (0.6 mL), 1.5 M NaOMe in MeOH (0.16 mL, 0.08 mmol) was added. The resulting mixture was stirred for 10 min, concentrated, and dried under reduced pressure to obtain the title compound 8. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.36 (d, J=8.6 Hz, 1H), 7.92-8.04 (m, 3H), 7.67-7.82 (m, 4H), 7.55 (t, J=7.6 Hz, 1H), 7.32 (d, J=4.4 Hz, 1H), 4.24-4.32 (m, 4H), 3.89 (t, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22H19N5O3: 402.2 (M+H). Found 402.4.

Workup

  1. concentrationconcentrated
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-877d75f1e3ee4477887d05926b818631
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…