4-Amino-2,2,6,6-tetramethylpiperidine → HCID 11952414, compound

HRID 2243672Notes

Reaction equation

HRID 2243672 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][C:47]([CH3:50])([CH3:49])[NH:46][C:45]([CH3:52])([CH3:51])[CH2:44]1>CN(C=O)C>[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]([NH:42][CH:43]3[CH2:44][C:45]([CH3:52])([CH3:51])[NH:46][C:47]([CH3:50])([CH3:49])[CH2:48]3)[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]

Participants

4

Reactant 2

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 11950100HCID 11950100, compound

Product 1

HCID 11952414HCID 11952414, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (0.070 g, 0.107 mmol) was dissolved in DMF (1.5 mL) and treated with 4-amino-2,2,6,6-tetramethylpiperidine (62 ul, 0.361 mmol). Stirring at room temperature and heating to 70° C. under argon produced no reaction so the mixture was microwaved at 200° C. for 15 min. The solvent was removed in vacuo and the crude product was purified by flash chromatography on silica gel, eluting with CH2C2—10% MeOH/CH2C2. The product was repurified by the same method to afford the title compound as a white solid. mp (dec) 220° C.; LC-MS m/z 659 (M+H)+, 1.94 min (ret. time).

Workup

  1. temperatureheating to 70° C. under argon
  2. customproduced
  3. customno reaction so the mixture
  4. customwas microwaved at 200° C. for 15 min
  5. customThe solvent was removed in vacuo
  6. customthe crude product was purified by flash chromatography on silica gel
  7. washeluting with CH2C2—10% MeOH/CH2C2
  8. customThe product was repurified by the same method

Sources & evidence

ORD record
ord-95f2d0dd602e4700beeb4c1655e1d7e9
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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