2-Thiopheneacetic acid → 4-(1-Ethyl-propylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester

HRID 1750189

반응식

HRID 1750189 반응식
[S: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[S:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

참가 물질

8

반응물 4

HCID 159702-Thiopheneacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2회HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

생성물 1

HCID 867144044-(1-Ethyl-propylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester수율 77.2%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1.56 g of thiophen-2-yl-acetic acid in 25 ml of dry DMF 1.49 g of HOBT, 2.11 g of EDC and 2.6 ml of DIPEA were added at 0° C. After 30 min 2.36 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 2.6 ml of DIPEA 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 crystallization from diethylether to yield 2.78 g (77%) of 4-(1-ethyl-propylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester.

후처리

  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 crystallization from diethylether

출처 및 근거

ORD 기록
ord-9d62fa8528664bf799443549f7c934af
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156796B2

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