Triethylamine → HCID 58928973, 화합물

HRID 853655노트

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HRID 853655 반응식
[CH:1]([O:14][C:15]1[C:24]2[N:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:18]([C:25](O)=[O:26])=[C:17]2[CH2:28][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[C:30](=[O:31])[C:16]=12)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:43]([O:42][C:40]([N:47]1[CH2:48][CH2:49][N:50]([C:25]([C:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[N:23][C:24]=3[C:15]([O:14][CH:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:16]3[C:30](=[O:31])[N:29]([CH2:32][C:33]4[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=4)[CH2:28][C:17]=23)=[O:26])[CH2:51][CH2:52]1)=[O:41])([CH3:46])([CH3:45])[CH3:44]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58928692HCID 58928692, 화합물

생성물 1

HCID 58928973HCID 58928973, 화합물수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Carboxylic acid 213 (0.015 g, 0.029 mmol) was dissolved in 0.8 mL of dimethylformamide. To this was added BOC-piperazine (0.0116 g, 0.058 mmol), triethylamine (0.012 mL, 0.087 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.011 g, 0.058 mmol), 1-Hydroxybenzotriazole hydrate (0.0059 g, 0.0435 mmol) and stirred at room temperature. After 15 hours, starting material was consumed. Dilute with dichloromethane, washed with 1M HCl solution, saturated brine solution, dried (Na2SO4), concentrated to give crude product. Chromatographed (10 to 50% ethyl acetate/hexanes) to give 4-[9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester 229 (0.009 g, 0.013 mmol, 45%.) 1H NMR (CDCl3) 9.075 (s, 1H), 8.15 (s, 1H), 8.03 (d, 1H), 7.74 (dd, 4H), 7.53 (dd, 1H), 7.27 (m, 8H), 7.04 (dd, 2H), 4.91 (d, J=17 Hz, 1H), 4.69 (d, J=17 Hz, 1H), 4.41 (d, J=17 Hz, 1H), 4.055 (d, J=17 Hz, 1H), 3.55-2.96 (br m, 8H), 1.44 (s, 9H.) MS: 687 (M+1).

후처리

  1. customwas consumed
  2. additionDilute with dichloromethane
  3. washwashed with 1M HCl solution, saturated brine solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give crude product
  7. customChromatographed (10 to 50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-14f4350fc0dd45fc8fc94bac0a98cadc
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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