Water → HCID 68819643, compound

HRID 508616Notes

Reaction equation

HRID 508616 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:8]([C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:27])(=[O:26])[NH2:25])=[CH:20][CH:19]=2)[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:3][CH2:4][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:8]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH2:25])(=[O:26])=[O:27])=[CH:20][CH:19]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 17755035HCID 17755035, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68819643HCID 68819643, compoundYield 798%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3c (4 g, 1.04 mmol) in 20 mL of THF was added LiAlH4 (1.26 g, 33.2 mmol). The reaction mixture was stirred for 6 hours at room temperature. EtOAC (30 mL) and water (30 mL) were added successively. The solvent was removed in vacuo and the resulting solid was filtered. The crude product was purified by column chromatography (EtOAc/Hexanes in adequate proportions) to give the compound (2.85 g, 80%) as a white solid. mp 165.9-169.3° C. 1H NMR (300 MHz, DMSO-d6): δ 7.81 (d, J=9 Hz, 2H), 7.48-7.43 (m, 2H), 7.41 (d, J=9 Hz, 2H), 7.21 (d, J=8 Hz, 2H), 7.14 (d, J=8 Hz, 2H), 6.59 (s, 1H), 5.26 (t, J=6 Hz, 1H), 4.51 (d, J=6 Hz, 2H), 2.31 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customThe crude product was purified by column chromatography (EtOAc/Hexanes in adequate proportions)

Sources & evidence

ORD record
ord-313846c440874bbaaa4a13a60bda51ea
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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