Water → HCID 67326247, compound

HRID 2199313Notes

Reaction equation

HRID 2199313 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[C:17]([C:29]([F:32])([F:31])[F:30])[CH:16]=2)=[CH:9][C:3]=1[C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(OCC)C>[OH:5][CH2:4][C:3]1[CH:9]=[C:10]([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]3)=[C:17]([C:29]([F:32])([F:30])[F:31])[CH:16]=2)[CH:11]=[CH:12][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 67347178HCID 67347178, compound

Product 1

HCID 67326247HCID 67326247, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution Ethyl 2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)benzoate (300 mg, 0.65 mmol) in dried THF (2.2 mL) was added Lithium aluminium hydride 2.0M THF solution (0.48 mL, 0.98 mmol) at 0° C. The reaction mixture was stirred for 2 hours at room temperature. When the reaction was completed, the reaction mixture was diluted with ethyl ether (2.0 mL) and added water very slowly to decompose the excess of the reagent. To a reaction mixture was added MgSO4, celite filtered and concentrated under reduced pressure. The title compound (230 mg, 84% yield) was used next step without further purification. MS m/z: 422 [M+1].

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac3fff0521a449d9b2b8851618c4571a
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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