1-Hydroxybenzotriazole → HCID 86714418, 화합물

HRID 1750207

반응식

HRID 1750207 반응식
[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

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2회HCID 44267162-(5-chlorothiophen-2-yl)acetic AcidHCID 61311526HCID 61311526, 화합물

생성물 1

HCID 86714418HCID 86714418, 화합물수율 90%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd67a932963d4c55a2a26753a700da1d
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156796B2

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