Hydrochloric Acid → HCID 178523279, compound

HRID 412691Notes

Reaction equation

HRID 412691 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:34]=[CH:33][C:16]2[NH:17][C:18]([CH2:20][C:21]3[NH:25][C:24]4[CH:26]=[CH:27][C:28]([C:30](O)=[O:31])=[CH:29][C:23]=4[N:22]=3)=[N:19][C:15]=2[CH:14]=1.O.ON1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2N=N1.CN1CCOCC1.N#N.C1(C[CH2:62][CH2:63][CH2:64][NH2:65])C=CC=CC=1.Cl.[Na+].[Cl-]>CN(C)C=O.C(O)C.C(OCC)(=O)C>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]1[CH:34]=[CH:33][C:16]2[NH:17][C:18]([CH2:20][C:21]3[NH:25][C:24]4[CH:26]=[CH:27][C:28]([C:30]([NH:65][CH2:64][CH2:63][CH2:62][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[O:31])=[CH:29][C:23]=4[N:22]=3)=[N:19][C:15]=2[CH:14]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 83242BenzenebutanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 178524164HCID 178524164, compound

Product 1

HCID 178523279HCID 178523279, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

2-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-1H-benzoimidazole-5-carboxylic acid (0.05g, 0.111 mmol) was dissolved in anhydrous dimethylformamide (0.5 mL) and the solution was combined with 1-hydroxybenzotriazole hydrate (0.017 g, 0.126 mmol), benzotriazole-1-yloxytrispyrrolidinophosphoniurnhexafluoro-phosphate (0.063 g, 0.121 mmol) and N-methylmorpholine (0.013 mL, 0.118 mmol) at room temperature under an atomosphere of dry N2. After 2 minutes 4-phenylbutylamine (0.02 mL, 0.127 mmol) was added and the mixture was stirred at room temperature for 2 hours. The mixture was transferred to a sparatory funnel containing 20% ethanol/ethyl acetate solution (7 mL), 0.2N HCl (3.5 mL) and saturated aqueous NaCl (3.5 mL). The aqueous phase was extracted once with 20% ethanol/ethyl acetate solution (7 mL) and the combined organic phases were washed with a solution containing 0.2N HCl (3.5 mL) in saturated aqueous NaCl (3.5 mL) followed by a final washing with saturated aqueous sodium bicarbonate solution (7 mL). The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated to dryness on a rotary evaporator to provide 2-[5-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-N-(3-phenylpropyl)-1H-benzoimidazole-5-carboxamide as crude material (0.14 g).

Workup

  1. customThe mixture was transferred to a sparatory funnel
  2. extractionThe aqueous phase was extracted once with 20% ethanol/ethyl acetate solution (7 mL)
  3. washthe combined organic phases were washed with a solution
  4. additioncontaining 0.2N HCl (3.5 mL) in saturated aqueous NaCl (3.5 mL)
  5. washa final washing with saturated aqueous sodium bicarbonate solution (7 mL)
  6. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-cf8ffe55bb7c484681f013ed64c1e02b
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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