Aluminium lithium hydride → HCID 50995630, compound

HRID 1404119Notes

Reaction equation

HRID 1404119 reaction equation
[CH3:1][N:2]([CH3:25])[C:3](=O)[CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:21])[CH:10]=[C:11]([CH2:16][CH2:17][C:18]([NH2:20])=O)[C:12]=2[O:14][CH3:15])[N:7]([CH2:22][CH3:23])[CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:21])[CH:10]=[C:11]([CH2:16][CH2:17][CH2:18][NH2:20])[C:12]=2[O:14][CH3:15])[N:7]([CH2:22][CH3:23])[CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58304040HCID 58304040, compound

Product 1

HCID 50995630HCID 50995630, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 28-3 (100 mg, 0.28 mmol) in THF (10 mL) was added lithium aluminum hydride (44 mg, 1.15 mmol) in portions. The mixture was stirred at room temperature overnight. NaSO4.10H2O was added, then the mixture was filtered and the filtrate was evaporated. The crude product was purified by preparative HPLC (acid conditions) to afford 28-4 (10 mg, 11%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 6.83 (s, 1H), 6.66 (d, J=6.6 Hz, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.80 (s, 3H), 3.04 (t, J=7.2 Hz, 2H), 2.77-2.69 (m, 6H), 2.62-2.60 (br.s, 2H), 2.40 (s, 6H), 1.85-1.78 (m, 2H), 1.42 (t, J=6.8 Hz, 3H). LRMS: calc 321.4 and found: 322.0 [M+1].

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe crude product was purified by preparative HPLC (acid conditions)

Sources & evidence

ORD record
ord-b19f92dc3f244c009a3d147601459b66
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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