Methanol → (S)-methyl 2-(4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate

HRID 1750983노트

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HRID 1750983 반응식
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[C@@H:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20].I[CH2:30][CH2:31][CH2:32][N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[NH:35][C:34]1=[O:42].C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O.ClCCl.O>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:30][CH2:31][CH2:32][N:33]3[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[NH:35][C:34]3=[O:42])[CH2:10][CH2:11]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[C@@H:18]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:19]([O:21][CH3:22])=[O:20]

참가 물질

8

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 13564030HCID 13564030, 화합물HCID 66652128(S)-methyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate

생성물 1

HCID 66652239(S)-methyl 2-(4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate수율 11.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
65 °C

실험 절차

A mixture of (S)-methyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)-2-phenylacetate (159 mg, 0.383 mmol, 1 equiv), 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (115.6 mg, 0.38 mmol, 1 equiv) and potassium carbonate (158.6 mg, 1.148 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. The reaction was cooled to ambient temperature and worked up using 5% methanol in dichloromethane and water. The organic layer was dried over MgSO4, and concentrated in vacuo. The crude mixture was purified using preparatory thin layer chromatography in 7% methanol in dichloromethane. The purified extract was lyophilized to afford the title compound as a white solid (25 mg, <10%); 1H NMR (400 MHz, DMSO-d6): δ 1.61 (bs, 2H), 1.84 (bs, 2H), 2.46 (bs, 4H); 2.50-2.51 (m, 4H); 3.74 (s, 3H); 3.85 (t, 2H, J=7.2 and 6.4 Hz); 4.15 (d, 1H, J=4.8 Hz); 4.80 (d, 1H, J=4.8 Hz); 5.89 (s, 1H)); 6.79-6.85 (m, 3H); 6.97 (d, 3H, J=2.8 Hz); 7.16-7.18 (m, 1H); 7.23 (t, 2H, J=7.2 and 8.8 Hz); 7.39-7.46 (m, 5H); 10.82 (s, 1H); MS for C32H35N5O4 m/z 554.11 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture was purified
  5. extractionThe purified extract

출처 및 근거

ORD 기록
ord-ca29b6eaa956461f975e0398dcb26843
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156840B2

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