Water → HCID 66795498, compound

HRID 1944815Notes

Reaction equation

HRID 1944815 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH2:23][NH:24][C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1.O>CCOCC.ClCCl.CO.C(N(CC)CC)C.ClCCl.CO.ClCCl>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:24][C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 66795949HCID 66795949, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 66795498HCID 66795498, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolventHCID 21913430dichloromethane MeOH Et3NSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.56 g (3.60 mmol) of N-[(6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridin-2-yl)methyl]-2,4,6-trimethylaniline in 30 ml of THF 14.5 ml (10.7 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The resulting mixture was heated to room temperature and then stirred for 10 min. Further on, 2 ml of water was added, and the resulting mixture was poured into 50 ml of water. The crude product was extracted with 3×30 ml of ether. The organic extract was washed with water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane, then dichloromethane-methanol 20/1 vol., then dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 1.66 g (90%) of orange oil. Anal. calc. for C36H39N3: C, 84.17; H, 7.65; N, 8.18. Found: C, 84.31; H, 7.77; N, 8.05. For 1H NMR (in CDCl3) see FIG. 1—Top spectrum.

Workup

  1. temperatureThe resulting mixture was heated to room temperature
  2. stirringstirred for 10 min
  3. extractionThe crude product was extracted with 3×30 ml of ether
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um

Sources & evidence

ORD record
ord-51aec5ff316044acb32aa1035023833f
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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