Aluminium lithium hydride → HCID 10403856, compound

HRID 2377680Notes

Reaction equation

HRID 2377680 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][C@@H:17]3[CH2:19][C@H:14]1[CH2:15][N:16]3[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=O)=[CH:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][N:13]1[CH2:18][C@@H:17]3[CH2:19][C@H:14]1[CH2:15][N:16]3[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[CH:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69205267HCID 69205267, compound

Product 1

HCID 10403856HCID 10403856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 15C in THF solution (30 mL) was treated with LAH (5.50 mmol) and stirred at room temperature for 2 hours. The mixture was treated with Na2SO4 decahydrate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (10% MeOH/CH2Cl2) to provide the title compound. The maleate salt was formed and recrystallization from ethanol/diethyl ether. 1H NMR (CD3OD, 300 MHz) δ 2.22-2.36 (m, 2H), 3.45-3.62 (m, 2H), 3.70 (s, 2H), 4.45-4.58 (m, 3H), 4.95 (s, 1H), 6.23 (s, 1H), 6.62-6.65 (m, 1H), 6.70 (t, J=3.0 Hz, 1H), 6.95 (dt, J=2.0, 6.0 Hz, 1H), 7.22 (dd, J=2.0, 8.0 Hz, 1H), 7.40-7.45 (m, 1H), 7.60 (t, J=2.0 Hz, 1H), 8.05 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 322 (M+H)+. Mp 211-214° C. Anal. Calcd for C19H19N4F.1.3 C4H4O4: C, 61.82;H, 5.36; N, 11.38. Found: C, 61.88;H, 4.99; N, 11.28.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-977ceaa5d6f342ea94105e28b0c2cce6
Source dataset
uspto-grants-2008_12
Patent number
US07470691B2

Reaction notes

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