1,2-Dichloroethane → 1-(2,2-Diphenylethyl)-3-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine

HRID 365451노트

반응식

HRID 365451 반응식
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15](O)=[O:16])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([C:26]1[CH:40]=[CH:39][C:29]([CH2:30][N:31]2[C:35]([CH2:36][CH2:37][NH2:38])=[CH:34][N:33]=[CH:32]2)=[CH:28][CH:27]=1)#[N:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15](=[O:16])[NH:38][CH2:37][CH2:36][C:35]3[N:31]([CH2:30][C:29]4[CH:39]=[CH:40][C:26]([C:24]#[N:25])=[CH:27][CH:28]=4)[CH:32]=[N:33][CH:34]=3)[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 158510473-(4-Cyanobenzyl) histamineHCID 232911301-(2,2-Diphenylethyl)-3-carboxy piperidine

생성물 1

HCID 179300651-(2,2-Diphenylethyl)-3-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-(2,2-Diphenylethyl)-3-carboxy piperidine(472 mg, 1,52 mmol),3-(4-cyanobenzyl) histamine (456 mg, 1.52 mmol) (EXAMPLE 1, Step E) HOBT (216 mg, 1.60 mmol), EDC (307 mg, 1.60 mmol), and Et3N (637 uL, 4.57 mmol) were dissolved in DMF (10 mL) and was stirred overnight at ambient temperature. The solution was concentrated under reduced pressure and chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH) to give the title compound 1H NMR (CDCl3) δ 7.96 (br s, 1H), 7.60 d, 2H, J=8 Hz), 7.46 (s, 1H), 7.09-7.37 (m, 12H), 6,74 (s, 1H), 5.20 (s, 2H), 4.26 (t, 1H, J=8 Hz), 3.05-3.17 (m, 2H), 2.93-3.04 (m,1H), 2.78-2.91 (m,2H), 2.49-2,61 (m 1H), 22.40-2.47 (m, 1H), 2.15-2.30 (m, 2H), 1.95-2.14 (m, 2H), 1.86 (d, 1H, J=12 Hz), 1.29-1.55 (m, 3H). FAB MS 518 (M+1)

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. customchromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH)

출처 및 근거

ORD 기록
ord-9e79f8b6d889493aba103174744f693c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127366

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