4-(1-Pyrrolidinyl)piperidine → Ammonium Hydroxide

HRID 2243765Notes

Reaction equation

HRID 2243765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:34].[N:35]1([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][CH2:38][CH2:37][CH2:36]1>C1COCC1>[NH4+:9].[OH-:23].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([N:43]3[CH2:44][CH2:45][CH:40]([N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:41][CH2:42]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:34]

Participants

5

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208115HCID 59208115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,4-dimethylbenzamide (0.015 g, 0.031 mmol) was dissolved in THF (5 mL) and 4-(1-pyrrolidinyl)piperidine (0.024 g, 0.155 mmol) was added. The reaction mixture was stirred at room temperature for 4 days. The solvents were pumped off in vacuo, and the residue was flash chromatographed on silica gel (10 g) eluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2 ethanol:NH4OH to give the title compound as a white amorphous solid. mp (dec) 189-194° C. LC-MS m/z 562 (M+H)+, 1.62 min (ret time).

Workup

  1. customchromatographed on silica gel (10 g)
  2. washeluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2 ethanol

Sources & evidence

ORD record
ord-e74481b47c72463db69593aab3a1d34d
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…