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Sodium Bicarbonate → HCID 58415515, 화합물

HRID 46172
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HRID 46172 반응식
[Cl-].[NH2:2][CH2:3][C:4]1([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[NH+:13][CH:14]=[CH:15][N:5]12.[C:23]([O-:26])(O)=O.[Na+]>C(Cl)Cl>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([C:4]2([CH2:3][N:2]3[CH2:11][CH2:12][CH2:4][CH2:3][C:23]3=[O:26])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]3=[N:13][CH:14]=[CH:15][N:5]23)=[CH:17][CH:18]=1
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참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 178509337HCID 178509337, 화합물

생성물 1

HCID 58415515HCID 58415515, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred biphasic mixture of a solution of 5-(aminomethyl)-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-1-ium chloride (25 mg) in CH2Cl2 (3 mL) and aqueous saturated NaHCO3 (3 mL) was added a solution of 5-bromobutyryl chloride (34 mg) in CH2Cl2 (1 mL). After 30 minutes layers were separated. Organic layer was dried over Na2SO4 and concentrated. The residue was then dissolved in DMF (0.5 mL) and NaH (12 mg, 60% in mineral oil) was added and stirred for 30 minutes. The reaction was then quenched with water, diluted with DMF and filtered. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-55% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min) afforded title compound as a white solid. HRMS. Found, 408.0718; calcd for (M+H)+, 408.0706. 1H NMR (500 MHz, CDCl3): δ 7.98 (s, 1 H); 7.52-7.43 (m, 4 H); 7.39-7.34 (m, 2 H); 7.16 (d, J=1.54 Hz, 1 H); 7.13-7.09 (m, 2 H); 4.57 (d, J=14.04 Hz, 1 H); 4.38 (d, J=14.28 Hz, 1 H); 2.52-2.46 (m, 2 H); 2.09-1.95 (m, 2 H), 1.62 (p, J=7.47 Hz, 2 H).

후처리

  1. customAfter 30 minutes layers were separated
  2. dry with materialOrganic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionThe residue was then dissolved in DMF (0.5 mL)
  5. additionNaH (12 mg, 60% in mineral oil) was added
  6. customThe reaction was then quenched with water
  7. additiondiluted with DMF
  8. filtrationfiltered
  9. customPurification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-55% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min)

출처 및 근거

ORD 기록
ord-4ea957d5d60847e99c8f8ca0406f8d86
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541595B2

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