Ethyl Acetate → HCID 70944847, compound

HRID 1190890Notes

Reaction equation

HRID 1190890 reaction equation
[N:1]1([C:6]([C:8]2[CH:9]=[C:10]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[N:25]=[CH:24][CH:23]=3)[CH:11]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=O)[CH:13]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>C1COCC1>[N:1]1([CH2:6][C:8]2[CH:9]=[C:10]([NH:21][C:22]3[C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[N:25]=[CH:24][CH:23]=3)[CH:11]=[C:12]([CH2:14][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 70944817HCID 70944817, compound

Product 1

HCID 70944847HCID 70944847, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-{3,5-bis[(pyrrolidin-1-yl)carbonyl]phenyl}-7-chloroquinolin-4-amine (84 mg, 0.19 mmol) in 15 mL of anhydrous THF, was added portionwise LiAlH4 (71 mg, 10 eq). The reaction mixture was stirred at room temperature for 2 h and then 10 mL of ethyl acetate was added. The mixture was filtered through a celite pad. The filtrate was evaporated and the residue was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1) to yield expected compound (4 mg, 5%) as a yellow oil. m/z (ESI) 420.9 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. customThe filtrate was evaporated
  3. customthe residue was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1)

Sources & evidence

ORD record
ord-5d46165e830946b2b39724b7b57fac9a
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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