4-Piperidinamine → Ammonium Hydroxide

HRID 2243673Notes

Reaction equation

HRID 2243673 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]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=4)[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:41].[NH2:42][CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C1COCC1.CCOC(C)=O>[NH4+:9].[OH-:36].[NH2:42][CH:43]1[CH2:48][CH2:47][N:46]([C:16]2[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=4)[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]3[CH2:12][NH:11][C:10](=[O:41])[N:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[C:14]=3[N:15]=2)[CH2:45][CH2:44]1

Participants

6

Reactant 2

HCID 4243614-PiperidinamineHCID 11950100HCID 11950100, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11949762HCID 11949762, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-fluoro-4-methylbenzamide (0.080 g, 0.137 mmol) and 4-aminopiperidine (0.055 g, 0.551 mmol) were suspended in THF (3 mL) and stirred under argon for 3 days. The completed reaction mixture was diluted with EtOAc and the organic phase washed with water, brine (twice), dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel, eluting with 6:0.5:0.05 CH2Cl2:EtOH:NH4OH to afford the title compound as an off-white solid. mp 240° C.; LC-MS m/z 602 (M+H)+, 1.79 min (ret. time).

Workup

  1. customThe completed reaction mixture
  2. washthe organic phase washed with water, brine (twice),
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography on silica gel
  7. washeluting with 6:0.5:0.05 CH2Cl2

Sources & evidence

ORD record
ord-9d9cbde2f2a245648975f87047242726
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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