Sodium Hydroxide → HCID 21897070, compound

HRID 2055343Notes

Reaction equation

HRID 2055343 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]([CH2:22][OH:23])[CH2:20][OH:21])[N:3]=1.[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([NH:31][CH3:32])[CH2:27][CH2:26]1.[OH-].[Na+]>O1CCOCC1>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([N:31]([CH3:32])[CH:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)[N:3]=[C:4]([NH:18][CH:19]([CH2:22][OH:23])[CH2:20][OH:21])[N:5]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5663231-Methyl-4-(methylamino)piperidineHCID 21897072HCID 21897072, compound

Product 1

HCID 21897070HCID 21897070, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 131 (0.979 g, 0.271 mmol) dissolved in 3 mL 1,4-dioxane was added methyl-4-(methylamino)piperidine (0.05 mL, 0.34 mmol) dissolved in 2 mL 1,4-dioxane followed by the addition of 2.5 N NaOH (aq) (0.11 mL, 0.275 mmol). The mixture was heated at reflux for 3 h 45 min, cooled to about room temperature, and then concentrated under reduced pressure. The resulting material was diluted with dichloromethane and filtered. The filtrate was then concentrated affording 56.5 mg of material. The crude material was purified by silica gel pipet column eluting with 100% methanol affording an white solid 132 (21.1 mg, 18%), mp 84° C.; MS (ESI): m/z 454 (34.7), 452 (M+H, 100), 422 (11.3), 248 (25.3), 247 (51.3), 157 (60.3), 129 (27.5).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h 45 min
  3. temperaturecooled to about room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionThe resulting material was diluted with dichloromethane
  6. filtrationfiltered
  7. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-208bdaeb31c8476ab2a0e2777791935f
Source dataset
uspto-grants-2008_02
Patent number
US07332489B2

Reaction notes

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