Diisopropylethylamine → HCID 66622253, compound

HRID 852899Notes

Reaction equation

HRID 852899 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[NH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:31][CH:32]=3)[N:7]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 571728Methyl 4-(aminomethyl)benzoate2×HCID 22308410HCID 22308410, compound

Product 1

HCID 66622253HCID 66622253, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a sealed flask, a mixture of 7 (744 mg, 2.53 mmol), methyl 4-(aminomethyl)benzoate (628 mg, 3.80 mmol) and i-Pr2NEt (882 μl, 5.07 mmol) in isopropanol (50 mL) was heated to 120-125° C. for 7 days (during this period of time an excess of methyl 4-(aminomethyl)benzoate was added to the reaction mixture). The reaction mixture was allowed to cool to the room temperature, concentrated and purified by flash chromatography on silica gel (MeOH/CH2Cl2, 5/95→10/90 plus several drops of NH4OH) to afford the title compound 8 (671 mg, 1.59 mmol, 63% yield) as an orange sticky solid.

Workup

  1. additionwas added to the reaction mixture)
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2, 5/95→10/90 plus several drops of NH4OH)

Sources & evidence

ORD record
ord-a0eb6a9b9f23484e8b9cab0011c1c028
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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