2-Thiopheneacetic acid → 3-(2-Thiophen-2-yl-acetylamino)-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester

HRID 1750242ノート

反応式

HRID 1750242 の反応式
[S: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:50])[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[C:45]([F:48])([F:47])[F:46])=[C:34]([NH2:49])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:50])[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[C:45]([F:48])([F:46])[F:47])=[C:34]([NH:49][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 81531DiisopropylethylamineHCID 181649HOAtHCID 86714449HCID 86714449、化合物

生成物 1

HCID 867144503-(2-Thiophen-2-yl-acetylamino)-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester収率 100%

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 0.71 g of thiophen-2-yl-acetic acid in 10 ml of dry DMF 0.68 g of HOAT, 1.22 g of EDC and 2.25 ml of DIPEA were added at 0° C. After 30 min 1.44 g of 3-Amino-4-(2-trifluoromethyl-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 2.00 g (100%) of 3-(2-Thiophen-2-yl-acetylamino)-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester, which was used without further purification.

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

出典と根拠

ORDレコード
ord-695c0b17759b4978aed2026212961a4d
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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