Water → HCID 58392374, compound

HRID 561604Notes

Reaction equation

HRID 561604 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:10][C:11](OCC)=[O:12])=[C:4]([F:28])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(#N)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([F:28])[C:5]([CH:9]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:10][CH2:11][OH:12])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 58392239HCID 58392239, compound

Product 1

HCID 58392374HCID 58392374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 1.09 g (2.56 mmol) of the compound from Example 102A in 6 ml of tetrahydrofuran was added dropwise to 9.0 ml (9.0 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 12 ml of tetrahydrofuran at RT under argon. The mixture was stirred at 60° C. for 1 h and then water and acetonitrile were added, and the suspension was filtered through kieselguhr. The solvents were removed in a rotary evaporator, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 0.88 g (90% of theory) of the title compound was obtained.

Workup

  1. filtrationthe suspension was filtered through kieselguhr
  2. customThe solvents were removed in a rotary evaporator
  3. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-e65736da9ba1413facf877cd8a652757
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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