1,4'-Bipiperidine → Ammonium Hydroxide

HRID 2243766Notes

Reaction equation

HRID 2243766 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:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C1COCC1>[NH4+:9].[OH-:23].[N:35]1([CH:41]2[CH2:46][CH2:45][N:44]([C:16]3[N:17]=[C:18]([C:19]4[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=4[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]4[CH2:12][NH:11][C:10](=[O:34])[N:9]([C:3]5[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=5[F:8])[C:14]=4[N:15]=3)[CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 2

HCID 786071,4'-BipiperidineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208132HCID 59208132, 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 1,4′-bipiperidine (0.026 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) 179-184° C. LC-MS m/z 576 (M+H)+, 1.54 min (ret time).

Workup

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

Sources & evidence

ORD record
ord-0f059af057204dae9a1630421bb6f0d7
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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