Triethylamine → HCID 58928973、化合物

HRID 853655ノート

反応式

HRID 853655 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 58928973HCID 58928973、化合物収率 45%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-14f4350fc0dd45fc8fc94bac0a98cadc
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

読み込み中…