4-Piperidinamine → Ammonium Hydroxide

HRID 2243658Notes

Reaction equation

HRID 2243658 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)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37].[NH2:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>CN(C=O)C>[NH4+:9].[OH-:28].[NH2:38][CH:39]1[CH2:44][CH2:43][N:42]([C:16]2[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]3[CH2:12][NH:11][C:10](=[O:37])[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)[CH2:41][CH2:40]1

Participants

5

Reactant 2

HCID 4243614-PiperidinamineHCID 11950096HCID 11950096, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952048HCID 11952048, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl}-3-thiophenecarboxamide, (0.027 g, 0.05 mmol) was dissolved in DMF (4 mL) and 4-aminopiperidine (0.1 g, 1.0 mmol) was added. The mixture was stirred under argon at room temperature for 17 h. The solvents were pumped off in vacuo. The residue was flash chromatographed on silica gel (10 g) eluted with CH2Cl2 followed by 6:0.25:0.025, CH2Cl2:isopropanol:NH4OH and then by 6:0.5:0.025 CH2Cl2: isopropanol:NH4OH to give the title compound as a white amorphous solid. This was crystallized from CH2Cl2/hexane to give the title compound as a white crystalline solid. mp (dec) 250-261° C.; LC-MS m/z 576 (M+H)+, 1.6 min (ret. time).

Workup

  1. customchromatographed on silica gel (10 g)
  2. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-5d4078e34b8a438581fcdf9524712757
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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