1,2-Dichloroethane → Ethyl (+/-)-10,11-dihydro-3-[[[(1H-benzimidazol-2-yl)methyl]methylamino]carbonyl]5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 613382노트

반응식

HRID 613382 반응식
[CH2:1](Cl)[CH2:2]Cl.[C:5]([C:8]1C=C[C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25]C=CC=3C[C:12]=2[CH:28]=1)(O)=[O:6].Cl.Cl.[CH3:31][NH:32][CH2:33][C:34]1[NH:35][C:36]2[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=2[N:38]=1.[CH:43]1[CH:44]=CC2N(O)N=N[C:47]=2[CH:48]=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH:38]1[C:37]2[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=2[N:35]=[C:34]1[CH2:33][N:32]([CH3:31])[C:5]([C:8]1[CH:28]=[CH:12][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:44]=[CH:43][C:48]=3[CH2:47][C:1]=2[CH:2]=1)=[O:6]

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13169407((1H-1,3-benzodiazol-2-yl)methyl)(methyl)amine dihydrochlorideHCID 15516628Ethyl (+/-)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate

생성물 1

HCID 54459000Ethyl (+/-)-10,11-dihydro-3-[[[(1H-benzimidazol-2-yl)methyl]methylamino]carbonyl]5H-dibenzo[a,d]cycloheptene-10-acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

EDC (202.4 mg, 1.06 mmol) was added all at once to a solution of ethyl (±)-10,11-dihydro-3-carboxy-5H-dibenzo[a,d]cycloheptene-10-acetate (285.6 mg, 0.88 mmol), 2-(methylamino)methylbenzimidazole dihydrochloride (247.2 mg, 1.06 mmol), HOBt.H2O (142.7 mg, 1.06 mmol), and diisopropylethylamine (0.61 mL, 3.52 mmol) in anhydrous DMF (4.4 mL) at RT. The reaction was stirred at RT for 16.5 h, then was concentrated on the rotavap (high vacuum). The residue was reconcentrated from xylenes, then was dissolved in H2O (5 mL). EtOAc extraction (2×5 mL), drying (MgSO4), concentration, and chromatography (silica gel, 5% MeOH in 1:1 EtOAc/CHCl3) gave the title compound as a faintly yellow foam (389.2 mg, 95%): TLC Rf (10% MeOH in 1:1 EtOAc/CHCl3) 0.60; 1H NMR (400 MHz, CDCl3) δ 7.70-7.80 (m, 1H), 7.40-7.50 (m, 1H), 7.35 (s, 1H), 7.21-7.32 (m, 3H), 7.04-7.21 (m, 5H), 4.76-4.88 (m, 2H), 4.36 (d, J=15.2 Hz, 1H), 4.18 (q, J=7.1 Hz, 2H), 3.90 (d, J=15.2 Hz, 1H), 3.82-3.95 (m, 1H), 3.38 (dd, J=15.4, 4.0 Hz, 1H), 3.11 (s, 3H), 3.03 (dd, J=15.4, 9.5 Hz, 1H), 2.69 (dd, J=15.8, 4.8 Hz, 1H), 2.52 (dd, J=15.8, 9.6 Hz, 1H), 1.27 (t, J=7.1 Hz, 3H); FTIR (CCl4) 2700-3470 (broad), 1735, 1629 (shoulder), 1617, 1484, 1454, 1422, 1397, 1271, 1180, 1157 cm-1 ; MS (ES) m/e 468.2 (M+H)+.

후처리

  1. customat RT
  2. concentrationwas concentrated on the rotavap (high vacuum)
  3. dissolutionwas dissolved in H2O (5 mL)
  4. extractionEtOAc extraction (2×5 mL)
  5. customdrying
  6. concentration(MgSO4), concentration, and chromatography (silica gel, 5% MeOH in 1:1 EtOAc/CHCl3)

출처 및 근거

ORD 기록
ord-b9d1d29a4e024eb584bf6dbba0c21b2a
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008213

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