N,N,N',N'-Tetramethylethylenediamine → HCID 21948140, compound

HRID 2215029Notes

Reaction equation

HRID 2215029 reaction equation
[CH3:1][C:2]1(C)[CH2:7][CH2:6]CC(C)(C)N1.[Li][CH2:12]CCC.CN([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])C.N([C:31]1[N:32]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:33]2[C:38]([C:39](=[O:41])[CH:40]=1)=[C:37]([CH3:42])[CH:36]=[C:35]([O:43][CH2:44][CH3:45])[N:34]=2)C1C=CC=CC=1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:44]([O:43][C:35]1[N:34]=[C:33]2[C:38]([C:39](=[O:41])[C:40]([CH3:31])=[C:23]([N:21]([CH3:22])[C:20]3[CH:19]=[CH:6][CH:7]=[CH:2][CH:1]=3)[N:32]2[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[C:37]([CH2:42][CH3:12])[CH:36]=1)[CH3:45]

Participants

8

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 130352,2,6,6-TetramethylpiperidineHCID 25517Ammonium ChlorideHCID 21948182HCID 21948182, compoundHCID 178418339Butyllithium

Product 1

HCID 21948140HCID 21948140, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-60 °C

Procedure

To a suspension of 2,2,6,6-tetramethylpiperidine (153 mg, 0.18 mL, 1.08 mmol) in THF (10 mL) at 0° C., was added n-BuLi via syringe (1.6 M, 0.68 mL, 1.08 mmol) and TMEDA. The reaction mixture was stirred for 1 h under argon. The reaction mixture was cooled to −60° C. using an acetone/dry ice bath and 2-anilino-7-ethoxy-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (100 mg, 0.269 mmol) was added via syringe as a solution in THF (5 mL). The mixture was stirred for 1 h. Mel was added via syringe and the reaction was allowed to warm to room temperature and stirred for 18 h. A saturated aqueous solution of NH4Cl (20 mL) and EtOAc (20 mL) was added, and the organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash chromatography using 7:3 to 100:0 EtOAc:Hex to give 3 products as follows:

Workup

  1. stirringThe mixture was stirred for 1 h
  2. additionMel was added via syringe
  3. temperatureto warm to room temperature
  4. stirringstirred for 18 h
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography
  9. customHex to give 3 products

Sources & evidence

ORD record
ord-9dfb14aea2f04142af9698dff046d79a
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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