Triethylamine → HCID 11949766, compound

HRID 2243676Notes

Reaction equation

HRID 2243676 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][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]1.C(N(CC)CC)C.O1CCOCC1>C1COCC1.CCOC(C)=O>[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][CH2:45][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:47][CH2:48]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([F:35])[CH:29]=4)=[O:36])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH2:12][NH:11][C:10]1=[O:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 12682914-Amino-1-Boc-piperidineHCID 11950100HCID 11950100, compound

Product 1

HCID 11949766HCID 11949766, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

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, (0.1 g, 0.172 mmol), 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.11 g, 0.549 mmol) and triethylamine (0.5 mL) were suspended in stirred THF (4 mL) and heated to 60° C. under argon for 4 days. Dioxane (4 mL) was added and the reaction warmed to 85° C. for 2 days and then 95° C. for 1 day. The reaction mixture was diluted with EtOAc and the organics were washed with water, brine (twice), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel, eluting with 10% EtOAc/CH2Cl2 —50% EtOAc/CH2Cl2 to afford the title compound as a white solid. LC-MS m/z 702 (M+H)+, 2.41 min (ret. time)

Workup

  1. temperaturethe reaction warmed to 85° C. for 2 days
  2. washthe organics were washed with water, brine (twice),
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography on silica gel
  7. washeluting with 10% EtOAc/CH2Cl2 —50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-995fea7f897647479345992f97bc9581
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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