Furan-2-acetic acid → 3-(2-Furan-2-yl-acetylamino)-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester

HRID 1750237Notes

Reaction equation

HRID 1750237 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]2[CH3:45])=[C:34]([NH2:46])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]2[CH3:45])=[C:34]([NH:46][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 75974Furan-2-acetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 613065513-Amino-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester

Product 1

HCID 867144453-(2-Furan-2-yl-acetylamino)-4-(2-methyl-cyclohexylamino)-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.26 g of 2-furyl-acetic acid in 15 ml of dry DMF 1.50 g of HOAT, 2.11 g of EDC and 8 ml of DIPEA were added at 0° C. After 30 min 1.31 g of 3-Amino-4-(2-methyl-cyclohexylamino)-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 to obtain 1.85 g (100%) of 3-(2-Furan-2-yl-acetylamino)-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester, which was used without further purification.

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

Sources & evidence

ORD record
ord-f165229e94b8415c988226c074d1bc76
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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