Water → HCID 10204684, compound

HRID 1374006Notes

Reaction equation

HRID 1374006 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([F:25])[CH:18]=2)[N:3]=1.[NH2:26][CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:33][CH3:34].[OH-].[Na+].O>O1CCOCC1.CC(C)=O>[OH-:23].[NH4+:3].[CH:10]1([CH2:9][NH:8][C:6]2[N:7]=[C:2]([NH:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3[CH2:33][CH3:34])[N:3]=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([F:25])[CH:18]=3)[N:5]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 21897055HCID 21897055, compound

Product 2

HCID 14923Ammonium HydroxideHCID 10204684HCID 10204684, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a sample of 125 (10.02 g, 27.3 mmol) dissolved in 1,4-dioxane (150 mL) was added a solution of 2-(aminomethyl)-1-ethylpyrrolidine (4.0 mL, 27.3 mmol) in acetone (10 mL) followed by addition of NaOH (11 mL, 2.5 N, 27.3 mmol) and 27 mL of water. The reaction mixture was allowed to stir at reflux for about 2 hours. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was concentrated on the rotary evaporator and the resulting solid was dried overnight under vacuum. Column chromatography (silica gel, 93:6:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded a light yellow solid, compound 126 (7.014 g, 56%), mp 72° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 8.5 min, 93.4% purity; MS (ESI): m/z 458 (M+H, 37.3), 362 (4), 250 (100), 230 (15.3), 229 (44.1).

Workup

  1. temperatureat reflux for about 2 hours
  2. extractionThe reaction mixture was extracted 3 times with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over potassium carbonate
  5. concentrationThe sample was concentrated on the rotary evaporator
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-1dc7baa77d2140458f8abc409c4c4aef
Source dataset
uspto-grants-2007_01
Patent number
US07163943B2

Reaction notes

Loading…