Diisopropylamine → HCID 11624326, compound

HRID 1839386Notes

Reaction equation

HRID 1839386 reaction equation
[Li+].CC([N-]C(C)C)C.[Li]CCCC.C(NC(C)C)(C)C.[NH:21]([C:28]1[N:29]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:30]2[C:35]([C:36](=[O:38])[CH:37]=1)=[C:34]([CH3:39])[CH:33]=[CH:32][N:31]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C[O:49]CC1>>[NH:21]([C:28]1[N:29]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:30]2[C:35]([C:36](=[O:38])[CH:37]=1)=[C:34]([CH2:39][OH:49])[CH:33]=[CH:32][N:31]=2)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 10131414HCID 10131414, compoundHCID 178418339Butyllithium

Product 1

HCID 11624326HCID 11624326, compoundYield 53%

Conditions

Temperature
-78 °C

Procedure

A solution of LDA (38.2 mmol, freshly prepared from n-BuLi and diisopropylamine) in THF (53 mL) was added to a cooled (−78° C.) and stirred suspension of 2-anilino-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (2.50 g, 7.64 mmol) in THF (100 mL). The resulting mixture was stirred for 1 h, and then oxygen gas was bubbled, through a flitted glass tube, into the bottom of the reaction vessel. The mixture was stirred overnight, with continued bubbling of oxygen with slow warming to room temperature. The reaction was quenched with water and 1M HCl (5 mL), and then extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated in vacuo to afford an orange solid which was recrystalized from EtOAc to obtain 2-anilino-5-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-one (1.38 g, 53%): LCMS RT: 2.01 min, MH+: 344.3, Rf=0.22 (95:5 CH2Cl2:MeOH).

Workup

  1. additionwas added to
  2. stirringThe resulting mixture was stirred for 1 h
  3. customoxygen gas was bubbled, through a flitted glass tube
  4. stirringThe mixture was stirred overnight
  5. customwith continued bubbling of oxygen
  6. temperaturewith slow warming to room temperature
  7. customThe reaction was quenched with water and 1M HCl (5 mL)
  8. extractionextracted with CH2Cl2
  9. dry with materialThe organic phase was dried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto afford an orange solid which
  12. customwas recrystalized from EtOAc

Sources & evidence

ORD record
ord-a02160fde3d54d50b6677f0499c8bf7e
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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