Diisopropylethylamine → HCID 86714423, compound

HRID 1750212Notes

Reaction equation

HRID 1750212 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[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][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:33]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 37174621H-Pyrazol-1-ylacetic acidHCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Product 1

HCID 86714423HCID 86714423, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.76 g of Pyrazol-1-yl-acetic acid in 20 ml of dry DMF 2.09 g of HOAT, 3.75 g of EDC and 6.9 ml of DIPEA were added at 0° C. After 30 min 3.3 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were added and the reaction was stirred at rt 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 heptane to yield 2.28 g (47%) of 4-(1-Ethyl-propylamino)-3-(2-pyrazol-1-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 heptane

Sources & evidence

ORD record
ord-46a0fd65e85b4c668f72f27a7ad43e38
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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