Sodium Bicarbonate → HCID 58415515, compound

HRID 46172Notes

Reaction equation

HRID 46172 reaction equation
[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

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178509337HCID 178509337, compound

Product 1

HCID 58415515HCID 58415515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4ea957d5d60847e99c8f8ca0406f8d86
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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