Water → HCID 68292910, compound

HRID 1504954Notes

Reaction equation

HRID 1504954 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C[Al](C)C.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19](OC)=O)=[CH:12][CH:11]=1.O>C1(C)C=CC=CC=1.CO.C(Cl)Cl>[NH:3]1[CH2:2][CH2:1][N:4]=[C:19]1[CH2:18][CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH2:9])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 88628Methyl 4-aminobenzenebutanoateHCID 16682925Trimethylaluminum

Product 1

HCID 68292910HCID 68292910, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Ethylenediamine (6.23 mL, 93.1 mmol) was added dropwise to a stirred solution of AlMe3/Tol (58 mL, 2M), so that the temperature did not exceed −20° C. The reaction mixture was stirred at room temperature for 10 min, then to the mixture was added dropwise a solution of the compound 27 (4.5 g, 23.3 mmol) in Toluene (290 mL). The reaction mixture was stirred at 120° C. for overnight. After cooling, the solution was treated dropwise with water, diluted DCM and CH3OH and filtered with over MgSO4. The filtrate was concentrated and purified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2) to give the compound 55 (4.5 g, 96%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ6.96 (d, 2H, J=8.3 Hz), 6.62 (d, 2H, J=8.3 Hz), 3.56 (s, 4H), 2.55 (t, 2H, J=7.4 Hz), 2.23 (d, 2H, J=7.4 Hz), 1.84-1.94 (m, 2H).

Workup

  1. customdid not exceed −20° C
  2. stirringThe reaction mixture was stirred at 120° C. for overnight
  3. temperatureAfter cooling
  4. filtrationfiltered with over MgSO4
  5. concentrationThe filtrate was concentrated
  6. custompurified with silica gel column chromatography (EtOAc:CH3OH:TEA=3:1:0.2)

Sources & evidence

ORD record
ord-c77f9c0b29fc49f1b538863ecc9225ce
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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