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Water → tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

HRID 1046997
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HRID 1046997 반응식
[N:1]1[CH:2]=[C:3]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.C1C=C[NH+]=CC=1.[Br:43][Br-]Br.C(OCC)(=O)C.O>C1COCC1>[Br:43][C:2]1[N:1]=[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][C:6]3[N:15]=[CH:16][CH:17]=[CH:18][C:5]=3[N:4]2[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:26][CH2:27][CH2:28]2)=[CH:21][CH:20]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 69087639tert-butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

생성물 1

HCID 136331865tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate수율 59.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
3회

실험 절차

tert-Butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (9.8 g, 20.4 mmol) was dissolved in THF (350 mL). A solution of pyridinium bromide perbromide (6.5 g, 20.4 mmol) in THF (50 mL) was added to the mixture at −78° C. After three hours stirring at r.t., pyridinium bromide perbromide (2.6 g, 8.2 mmol) in THF was added to the mixture and the mixture was stirred at rt overnight. The mixture was poured into ethyl acetate (1.5 L) and mixed with water and separated. The combined organic phase was washed with saturated sodium bicarbonate solution in water, then dried with anhydrous sodium sulfate and evaporated. The residue was purified with silica gel column chromatography (dichloromethane/ethyl acetate, 20:1) to give the titled compound as a white solid (6.8 g, 59%). 1HNMR (CDCl3) 400 MHz δ: 8.04 (d, J=8.0 Hz, 2H), 7.40 (d, J=7.4 Hz, 2H), 7.31 (t, J=7.4 Hz, 1H), 7.23 (d, J=6.9 Hz, 2H), 7.12 (t, J=7.7 Hz, 1H), 6.94 (d, J=8.0 Hz, 1H), 6.88-6.80 (m, 1H), 6.66-6.62 (m, 1H), 6.29 (s, 1H), 5.10 (s, 1H), 2.58-2.37 (m, 4H), 2.18-2.08 (m, 1H), 1.94-1.84 (m, 1H), 1.39 (br s, 9H); LC/MS [M+H]: 558

후처리

  1. stirringthe mixture was stirred at rt overnight
  2. customseparated
  3. washThe combined organic phase was washed with saturated sodium bicarbonate solution in water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified with silica gel column chromatography (dichloromethane/ethyl acetate, 20:1)

출처 및 근거

ORD 기록
ord-13e1f53446f64865b19f1d1dc3360845
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569331B2

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