4-Piperidinamine → Ammonium Hydroxide

HRID 2243662Notes

Reaction equation

HRID 2243662 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:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40].[NH2:41][CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C1COCC1>[NH4+:9].[OH-:23].[NH2:41][CH:42]1[CH2:47][CH2:46][N:45]([C:16]2[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]3[CH2:12][NH:11][C:10](=[O:40])[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)[CH2:44][CH2:43]1

Participants

5

Reactant 2

HCID 4243614-PiperidinamineHCID 11950098HCID 11950098, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952052HCID 11952052, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide, (0.056 g, 0.1 mmol) was dissolved in THF (5 mL) and 4-aminopiperidine (0.2 g, 2.0 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 (15 g) eluted with 6:1:0.1, CH2Cl2:isopropanol:NH4OH to give the title compound as a white amorphous solid. m.p. (dec) 210-266° C.; LC-MS m/z 584 (M+H)+, 1.68 min (ret. time).

Workup

  1. customchromatographed on silica gel (15 g)
  2. washeluted with 6:1:0.1, CH2Cl2

Sources & evidence

ORD record
ord-c221be6e07a141c1ac5ceec266391f48
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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