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Diisopropylethylamine → 3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid 3,4,5-trimethoxy-benzylamide

HRID 1823309
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HRID 1823309 반응식
[CH3:1][C:2]1[O:3][N:4]=[C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[N:8]([CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([OH:23])=O)[CH2:16]3)[C:7](=[O:24])[C:6]=12.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:56][O:57][C:58]1[CH:59]=[C:60]([CH:63]=[C:64]([O:68][CH3:69])[C:65]=1[O:66][CH3:67])[CH2:61][NH2:62]>CN(C)C=O>[CH3:69][O:68][C:64]1[CH:63]=[C:60]([CH:59]=[C:58]([O:57][CH3:56])[C:65]=1[O:66][CH3:67])[CH2:61][NH:62][C:21]([CH:17]1[CH2:18][CH2:19][CH2:20][CH:15]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[N:11][CH:10]=3)[C:5]3=[N:4][O:3][C:2]([CH3:1])=[C:6]3[C:7]2=[O:24])[CH2:16]1)=[O:23]
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참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 877363,4,5-TrimethoxybenzylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221701653-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid

생성물 1

HCID 69652763
3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid 3,4,5-trimethoxy-benzylamide
수율 86.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Combine 3-(3-methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexanecarboxylic acid (50 mg, 0.15 mmol) with 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride (32 mg, 0.17 mmol), 1-hydroxy-7-azabenzo-triazole (23 mg, 0.17 mmol), N,N-diisopropylethyl amine (44 mg, 3.4 mmol) and 3,4,5-trimethoxy benzylamine (33 mg, 0.17 mmol) in N,N-dimethyl-formamide (4 mL) and stir overnight at ambient temperature. Concentrate in vacuo and take up in water and extract with dichloromethane. Dry the combined extracts over sodium sulfate. Concentrate and chromatograph over silica gel to give 66 mg (85%) of the desired product as a white solid. MS(ES): (M+1)+ 507.2, 508.2, 509.2 m/z.

후처리

  1. concentrationConcentrate in vacuo
  2. extractionextract with dichloromethane
  3. dry with materialDry the combined extracts over sodium sulfate
  4. concentrationConcentrate

출처 및 근거

ORD 기록
ord-12428d4fa8114ee9b6bebc72afe7c4b2
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07037921B2

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