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

HRID 1750189ノート

反応式

HRID 1750189 の反応式
[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

参加物

8

反応物 4

HCID 159702-Thiopheneacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2 回HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d62fa8528664bf799443549f7c934af
出典データセット
uspto-grants-2015_10
特許番号
US09156796B2

反応ノート

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