Aluminium lithium hydride → HCID 49821053, compound

HRID 2407435Notes

Reaction equation

HRID 2407435 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH:11]([C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23]([Cl:29])[CH:22]=2)[CH:20]=1)[CH:12]1[CH2:14][CH2:13]1)[S:6]([CH2:9][CH3:10])(=[O:8])=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:29][C:23]1[CH:22]=[C:21]([C:19]2[CH:20]=[C:15]([CH:11]([N:5]([CH2:4][CH2:3][OH:2])[S:6]([CH2:9][CH3:10])(=[O:7])=[O:8])[CH:12]3[CH2:14][CH2:13]3)[CH:16]=[N:17][CH:18]=2)[CH:26]=[CH:25][C:24]=1[C:27]#[N:28]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 49820906HCID 49820906, compound

Product 1

HCID 49821053HCID 49821053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

A 40 mL scintillation vial was charged with ({[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-ethanesulfonyl-amino)-acetic acid methyl ester (130 mg, 0.290 mmol) in THF (5 mL). The reaction mixture was cooled to 78° C. and lithium aluminium hydride (1M in THF, 0.726 mL, 0.726 mmol) was added. The reaction was left to stir at −78° C. for 1 h. The reaction was quenched with water (1 mL), warmed to room temperature and concentrated in vacuo. The crude was dissolved in DMSO (4 mL) and purified using Xbridge C18 eluting with a 10 to 100% ACN-water to afford ethanesulfonic acid {[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-cyclopropyl-methyl}-(2-hydroxy-ethyl)-amide as a white solid.

Workup

  1. waitThe reaction was left
  2. customThe reaction was quenched with water (1 mL)
  3. temperaturewarmed to room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude was dissolved in DMSO (4 mL)
  6. custompurified
  7. washC18 eluting with a 10 to 100% ACN-water

Sources & evidence

ORD record
ord-588ea31c475c43faad7ca0c68181f368
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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