1-Hydroxybenzotriazole → HCID 86714415, compound

HRID 1750203Notes

Reaction equation

HRID 1750203 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C1C=CC2N(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:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 75974Furan-2-acetic acidHCID 81531Diisopropylethylamine2×HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Product 1

HCID 86714415HCID 86714415, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.48 g of 2-furylacetic acid in 30 ml of dry DMF 1.00 g of HOBT, 3.97 g of EDC and 1.8 ml of DIPEA were added at 0° C. After 30 min 3.50 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 1.8 ml of DIPEA 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 carbonate solution and saturated aqueous ammonium chloride solution, dried over magnesium sulphate and concentrated to obtain 4.44 g (87%) of 4-(1-Ethyl-propylamino)-3-(2-furan-2-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 carbonate solution and saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5b41ad70ccd4455b9fef9362a942927
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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