Water → HCID 67326247, compound

HRID 709304Notes

Reaction equation

HRID 709304 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-47f94959e3f040dda9a8f8ed48e1bb7c
Source dataset
uspto-grants-2015_11
Patent number
US09180127B2

Reaction notes

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