Pyridine → HCID 178478766, compound

HRID 1419232Notes

Reaction equation

HRID 1419232 reaction equation
N1C=CC=CC=1.[ClH:7].[O:8]1[CH2:13][CH2:12][N:11]([NH:14][N:15]=[CH:16][NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1.Cl.[C:28]([C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([CH2:41][C:42](=[O:44])[NH2:43])=[C:36](O)[CH:35]=[CH:34]2)(=[NH:30])[NH2:29].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)(=O)C>[ClH:7].[ClH:7].[O:8]1[CH2:13][CH2:12][N:11]([NH:14][N:15]=[CH:16][NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([O:24][C:36]3[CH:35]=[CH:34][C:33]4[C:38](=[CH:39][CH:40]=[C:31]([C:28](=[NH:29])[NH2:30])[CH:32]=4)[C:37]=3[CH2:41][C:42](=[O:44])[NH2:43])=[O:23])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178479747HCID 178479747, compound

Product 1

HCID 178478766HCID 178478766, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 131721204Methyl ethyl ketone acetic acid waterSolvent

Procedure

55 Milliliters of 10% hydrous pyridine was added to 1.5 g of 4-morpholinoaminoiminomethylamino-benzoic acid.hydrochloride, 1.12 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.55 g of DCC and 61 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of methanol, and the solution was added dropwise to 400 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. To the residue were added 20 ml of methanol and 2.07 ml of concentrated hydrochloric acid, and the solution was added dropwise to a mixed liquid of 200 ml of ether and 200 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.42 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom24 hours
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 15 ml of methanol
  7. additionthe solution was added dropwise to 400 ml of ether
  8. stirringby stirring for 24 hours
  9. temperatureunder cooling with ice
  10. filtrationThen, the precipitate was collected by filtration
  11. customto obtain a crude product
  12. customthe desired fractions were collected
  13. distillationthe solvent was distilled off under reduced pressure
  14. additionTo the residue were added 20 ml of methanol and 2.07 ml of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to a mixed liquid of 200 ml of ether and 200 ml of acetone
  16. stirringby stirring for 24 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-3940873ec88e4187b60245e26fd2550e
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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