Sodium Hydroxide → HCID 69484655, compound

HRID 1375486Notes

Reaction equation

HRID 1375486 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+].O1CCOC[CH2:36]1>>[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][CH2:16][CH3:36]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-Dioxane2×HCID 5663231-Methyl-4-(methylamino)piperidineHCID 21897072HCID 21897072, compound

Product 1

HCID 69484655HCID 69484655, compound

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-ce767e79cc1946809380a729fb08e2b3
Source dataset
uspto-grants-2007_01
Patent number
US07169785B2

Reaction notes

Loading…