Aluminium lithium hydride → HCID 58523977, compound

HRID 1958481Notes

Reaction equation

HRID 1958481 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23](OCC)=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[OH:24][CH2:23][C:21]1[N:22]=[C:17]2[C:16]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:15][C:14]([C:11]3[S:10][C:9]([N:8]([CH:34]([CH3:35])[CH3:36])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[N:13][CH:12]=3)=[CH:19][N:18]2[CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58208025Ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 58523977HCID 58523977, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 6-(2-(tert-butoxycarbonyl-(isopropyl)amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate (100 mg, 0.2 mmol) in ether was cooled in an ice bath and treated with solid LAH (15 mg, 0.4 mmol). The mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water, diluted with ethyl acetate and washed with water, brine and concentrated to give tert-butyl 5-(2-(hydroxymethyl)-8-phenylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl(isopropyl)carbamate. LCMS (Conditions C): 3.36 min (RT); (M+H)+=465.32 (100%).

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with ethyl acetate
  3. washwashed with water, brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb90ff9609cc483da2e6d6cc505de54c
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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