1-Hydroxybenzotriazole → HCID 86714418、化合物

HRID 1750207

反応式

HRID 1750207 の反応式
[Cl:1][C:2]1[S:6][C:5]([CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[C:35]([NH2:45])[CH:34]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:30][O:31][C:32](=[O:46])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][CH:40]([CH2:41][CH3:42])[CH2:43][CH3:44])=[C:35]([NH:45][C:8](=[O:10])[CH2:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:34]=1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2 回HCID 44267162-(5-chlorothiophen-2-yl)acetic AcidHCID 61311526HCID 61311526、化合物

生成物 1

HCID 86714418HCID 86714418、化合物収率 90%

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 1.00 g of 5-Chlorothiophen-2-yl-acetic acid in 15 ml of dry DMF 0.84 g of HOBT, 1.19 g of EDC and 1.5 ml of DIPEA were added at 0° C. After 30 min 1.33 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 1.5 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 2.00 g (89%) of 3-[2-(5-Chloro-thiophen-2-yl)-acetylamino]-4-(1-ethyl-propylamino)-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-bd67a932963d4c55a2a26753a700da1d
出典データセット
uspto-grants-2015_10
特許番号
US09156796B2

関連ノート

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