Water → 3-{4-[2-({[(4-biphenylsulfonyl)amino]carbonyl}amino)ethyl]phenyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

HRID 2077654노트

반응식

HRID 2077654 반응식
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Na+].[CH2:19]([C:21]1[N:31]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][NH:40][C:41](=O)[O:42]C3C=CC=CC=3)=[CH:34][CH:33]=2)[C:24]2=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]2[N:22]=1)[CH3:20].O>CN(C=O)C>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:41]([NH:40][CH2:39][CH2:38][C:35]2[CH:36]=[CH:37][C:32]([N:31]3[C:24]4=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]4[N:22]=[C:21]3[CH2:19][CH3:20])=[CH:33][CH:34]=2)=[O:42])(=[O:8])=[O:9])=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 50171404-Phenylbenzene-1-sulfonamideHCID 11384441Phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate

생성물 1

HCID 218756193-{4-[2-({[(4-biphenylsulfonyl)amino]carbonyl}amino)ethyl]phenyl}-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-biphenylsulfonamide (Greenlee, W. J.; Walsh, T. F.; et al. Eur. Pat. Appl., EP 617001 (1994), 56 mg, 0.24 mmol) in DMF (3 mL) was added NaH (60% oil dispersion, 20 mg, 0.5 mmol) at room temperature. After 5 min, phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate (step 1, 100 mg, 0.24 mmol) was added, and the mixture was stirred for an additional 1 h. The mixture was poured into water (50 mL) and extracted with diethyl ether (2×50 mL). The combined extracts were washed with water (50 mL), brine (50 mL) and dried (MgSO4). Removal of solvent gave white oily solids. Purification by preparative TLC (ethyl acetate) gave 66 mg (50%) of the title compound as a colorless oil: MS (ESI) m/z 554 (M+H)+; 1H-NMR (CDCl3) δ 8.06 (2H, d, J=8.6 Hz), 7.13 (2H, d, J=8.6 Hz), 7.60-7.53 (2H, m), 7.48-7.36 (3H, m), 7.21 (2H, d, J=8.4 Hz), 7.12 (2H, d, J=8.3 Hz), 6.92 (1H, s), 6.11 (1H, br.t, J=5.5 Hz), 3.54 (2H, dt, J=5.9, 6.0 Hz), 2.89 (2H, d, J=6.0 Hz), 2.64 (2H, q, J=7.5 Hz), 2.66 (3H, s), 2.40 (3H, s), 1.18 (3H, t, J=7.5 Hz).

후처리

  1. extractionextracted with diethyl ether (2×50 mL)
  2. washThe combined extracts were washed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customRemoval of solvent
  5. customgave white oily solids
  6. customPurification by preparative TLC (ethyl acetate)

출처 및 근거

ORD 기록
ord-793c4ea0937344aba85ca05af5f40b82
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928119B2

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