Diisopropylethylamine → HCID 86714423、化合物

HRID 1750212ノート

反応式

HRID 1750212 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 86714423HCID 86714423、化合物収率 47.4%

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 1.76 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.

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 precipitation from heptane

出典と根拠

ORDレコード
ord-46a0fd65e85b4c668f72f27a7ad43e38
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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