Sodium Methoxide → HCID 58189176, compound

HRID 1423204Notes

Reaction equation

HRID 1423204 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18](Cl)=[N:19]3)[CH2:11][CH2:10][N:9]1[CH2:27][C:28]([NH2:30])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][O-:32].[Na+]>CO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([O:32][CH3:31])=[N:19]3)[CH2:11][CH2:10][N:9]1[CH2:27][C:28]([NH2:30])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58188967HCID 58188967, compound

Product 1

HCID 58189176HCID 58189176, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred solution of (S)-2-(2-benzyl-4-(2-chloro-8-methoxyquinolin-5-yl)piperazin-1-yl)acetamide (40 mg, 0.1 mmol) in MeOH (1.2 mL) was treated with sodium methoxide (1.0 mL, 4.4 mmol) as a 25% solution in MeOH. The reaction mixture was allowed to stir for 18 h, then evaporated and purified by silica gel chromatography eluting with EtOAc to afford product as a yellow solid (23 mg, 55%). 1H NMR (MeOH-d4) 8.24-8.40 (br s, 1H), 7.10-7.24 (m, 5H), 7.03 (d, J=8.2, 1H), 6.94 (d, J=8.4, 1H), 6.82-6.88 (m, 1H), 4.03 (s, 3H), 3.97 (s, 3H), 3.42-3.56 (m, 1H), 2.94-3.27 (m, 8H), 2.64-2.85 (m, 2H). LC/MS 2.34 min, [M+1]+ 421.

Workup

  1. customevaporated
  2. custompurified by silica gel chromatography
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-14768227df3e466484089b3b6bb488da
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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