Diisopropylethylamine → HCID 86714425, compound

HRID 1750214Notes

Reaction equation

HRID 1750214 reaction equation
[O:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][CH:3]=[N:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[C:34]([NH2:44])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:40][CH3:41])[CH2:42][CH3:43])=[C:34]([NH:44][C:7](=[O:9])[CH2:6][C:5]2[O:1][N:2]=[CH:3][CH:4]=2)[CH:33]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 13042084isoxazol-5-yl-acetic acidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Product 1

HCID 86714425HCID 86714425, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.71 g of Isoxazol-5-yl-acetic acid in 15 ml of dry DMF 0.38 g of HOAT, 1.29 g of EDC and 3 ml of DIPEA were added at 0° C. After 30 min 1.32 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were added and the reaction was stirred at it for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by precipitation from diisoprpylether to yield 1.06 g (55%) of 4-(1-Ethyl-propylamino)-3-(2-isoxazol-5-yl-acetylamino)-benzoic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by precipitation from diisoprpylether

Sources & evidence

ORD record
ord-4f8d2823a07a477a86bd754f8de1385b
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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