Aluminium lithium hydride → HCID 86603190, compound

HRID 1818964Notes

Reaction equation

HRID 1818964 reaction equation
[OH:1][CH2:2][CH:3]([C:7]1[S:11][C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[O:14])=[N:9][CH:8]=1)[C:4]([NH2:6])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:6][CH2:4][CH:3]([C:7]1[S:11][C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=2)=[O:14])=[N:9][CH:8]=1)[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86603191HCID 86603191, compound

Product 1

HCID 86603190HCID 86603190, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 74.1 (0.08 mmol) in THF (1.0 mL) is added LAH (0.24 mL of 1.0 M solution in THF) and the reaction mixture is heated at 50° C. for 4 hours. The reaction is quenched with the dropwise addition of saturated NH4Cl, the volatiles are removed under reduced pressure and then extracted with EtOAc. The combined organic layers are filtered and concentrated to provide 1-[5-(2-amino-1-hydroxymethyl-ethyl)-thiazol-2-yl]-3-(3-trifluoromethyl-phenyl)-urea (compound 74.2) of sufficient purity for use in the next step.

Workup

  1. customThe reaction is quenched with the dropwise addition of saturated NH4Cl
  2. customthe volatiles are removed under reduced pressure
  3. extractionextracted with EtOAc
  4. filtrationThe combined organic layers are filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b8a779dbd1f47938f21b7d7fb568da2
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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