Aluminium lithium hydride → HCID 58724141, compound

HRID 2356210Notes

Reaction equation

HRID 2356210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22](O)=[O:23])[N:21]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][OH:23])[N:21]=2)[CH2:15][CH2:16]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58724173HCID 58724173, compound

Product 1

HCID 58724141HCID 58724141, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)thiazole-4-carboxylic acid (77 mg, 0.02 mmole) was dissolved in 1 mL of anhydrous THF under nitrogen protection. 0.4 mL of LiAlH4 (1.0M solution in THF) was added to the solution through a syringe at −78° C. After 30 minutes, the reaction mixture was quenched with MeOH, evaporated to dryness, and extracted with EtOAc and 0.1 N tartaric acid solution in water. The organic layer was then dried over Na2SO4, and the solvent was removed. The title compound was obtained in 77% yield after purification using preparative HPLC. 1H NMR (400 MHz, DMSO-D6) δ ppm 3.33 (M, 4 H), 3.47 (dd, J=6.19, 3.92 Hz, 4 H), 4.31 (s, 2 H), 6.63 (s, 1 H), 7.54-7.62 (m, 1 H), 7.65-7.75 (m, 2 H), 7.95-8.02 (m, 1H); ESI-MS: m/z 374.1 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with MeOH
  2. customevaporated to dryness
  3. extractionextracted with EtOAc and 0.1 N tartaric acid solution in water
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-8549b3c8cbc447bebf7f2c45c9a8c1bf
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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