N-(2-Furoyl)Glycine → Furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide

HRID 1178076

반응식

HRID 1178076 반응식
CCN(C(C)C)C(C)C.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:45]1([C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C.O>[O:21]=[C:19]([N:48]1[CH2:49][CH2:50][N:45]([C:51](=[O:52])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:60])[F:61])[CH2:46][CH2:47]1)[CH2:18][NH:17][C:15]([C:11]1[O:10][CH:14]=[CH:13][CH:12]=1)=[O:16]

참가 물질

8

반응물 5

HCID 21863N-(2-Furoyl)GlycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochloride

생성물 1

HCID 59559660Furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide수율 33%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (0.143 mL, 0.83 mmol) was added to a stirred solution of [(furan-2-carbonyl)-amino]-acetic acid (40 mg, 0.24 mmol) in DMF (1 mL). HOBT (38 mg, 0.28 mmol), EDCI.HCl (54 mg, 0.28 mmol) were added, followed by the addition of piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (0.2602 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (using silica gel, 60-120 A° and 10% methanol in chloroform as the eluent) afforded furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide in 33% yield. LC-MS purity: 83%, 1H NMR (CDCl3): δ 7.74 (d, 1H), 7.60 (m, 2H), 7.56 (d, 2H), 7.48 (s, 1H), 7.12 (t, 1H), 6.50 (q, 1H), 4.30 (m, 2H), 4.08-3.82 (m, 2H), 3.78-3.64 (m, 2H), 3.62-3.48 (m, 2H), 3.22 (m, 2H).

후처리

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification

출처 및 근거

ORD 기록
ord-47505f03ce0f49d981d333dcca6bfa28
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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