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Triethylamine → [3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1';3',1'']terphenyl-2'-yloxy]-ethanol

HRID 1884698
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HRID 1884698 반응식
[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:27]=[C:28]([CH:32]=[C:33]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=3)[C:34]=2[O:35][CH2:36][CH2:37]O)[C:29](O)=[O:30])[CH:23]=[CH:24][CH:25]=1.CCN(CC)CC.C1C=CC2N([OH:62])N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Cl:45][C:41]1[CH:40]=[C:39]([C:33]2[CH:32]=[C:28]([C:29](=[O:30])[NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[CH:27]=[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=3)[C:34]=2[O:35][CH:36]([OH:62])[CH3:37])[CH:44]=[CH:43][CH:42]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 222373953,5-Bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzoic acidHCID 222375078-Indol-1-yloctylamine

생성물 1

HCID 86583659[3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1';3',1'']terphenyl-2'-yloxy]-ethanol
수율 87.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a flame dried round bottom flask with 8-indol-1-yloctylamine (0.227 g, 0.930 mmol, preparation similar to step 1 of Example 54) in CH2Cl2 (10 mL) at room temperature was added 3,5-bis-(m-chlorophenyl)-4-(2-hydroxyethoxy)-benzoic acid (0.250 g, 0.620 mmol, prepared in step 2 of Example 55) followed by Et3N (0.259 mL, 1.86 mmol), HOBt (0.092 g, 0.682 mmol), and finally DCC (0.153 g, 0.744 mmol). After 3 days at this temperature, it was concentrated and then diluted with EtOAc (200 mL). The white solid (DCU) that formed was filtered off and washed with excess EtOAc. The organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (30 to 50% EtOAc/petroleum ether) to afford the product (0.341 g, 87%) as a solid; 1H NMR (CDCl3) δ 1.21-1.38 (m, 8H), 1.46-1.63 (m, 3H), 1.75-1.89 (m, 2H), 3.27-3.49 (m, 6H), 4.11 (t, J=8.1 Hz, 2H), 6.01-6.13 (m, 1H), 6.47 (d, J=2.2 Hz, 1H), 7.05-7.13 (m, 2H), 7.19 (t, J=8.8 Hz, 1H), 7.39-7.46 (m, 5H), 7.48-7.55 (m, 2H), 7.58-7.66 (m, 3H), 7.74 (s, 2H); mass spectrum [(+) ESI], m/z 629 (M)+.

후처리

  1. concentrationAfter 3 days at this temperature, it was concentrated
  2. additiondiluted with EtOAc (200 mL)
  3. customThe white solid (DCU) that formed
  4. filtrationwas filtered off
  5. washwashed with excess EtOAc
  6. washThe organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationAfter concentration
  9. customthe residue was purified by the Biotage Flash 40 apparatus (30 to 50% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-d51d5933805e4f729ee0f1c9659135a5
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06765021B2

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