2-Thiopheneacetic acid → 4-(2-Methyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester

HRID 1750225ノート

反応式

HRID 1750225 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: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[S:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

参加物

8

反応物 4

HCID 159702-Thiopheneacetic acidHCID 81531Diisopropylethylamine2 回HCID 181649HOAtHCID 613065513-Amino-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester

生成物 1

HCID 867144354-(2-Methyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-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 4.34 g of thiophen-2-yl-acetic acid in 40 ml of dry DMF 2.08 g of HOAT, 8.77 g of EDC and 13 ml of DIPEA were added at 0° C. After 30 min 8.00 g of 3-Amino-4-(2-methyl-cyclohexylamino)-benzoic acid methyl ester were added, followed by the addition of 6 ml of DIPEA and the reaction was stirred at rt for 48 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 11.75 g (100%) of 4-(2-Methyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-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-4edd78cc11eb44ab9666475fc2e18a80
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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