Pyridine → HCID 178511920, compound

HRID 1419236Notes

Reaction equation

HRID 1419236 reaction equation
N1C=CC=CC=1.Cl.Cl.[N:9]1([CH2:15][CH2:16][NH:17][N:18]=[CH:19][NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl.[C:31]([C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[C:40]([CH2:44][C:45](=[O:47])[NH2:46])=[C:39](O)[CH:38]=[CH:37]2)(=[NH:33])[NH2:32].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)=O>[N:9]1([CH2:15][CH2:16][NH:17][N:18]=[CH:19][NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][C:39]3[CH:38]=[CH:37][C:36]4[C:41](=[CH:42][CH:43]=[C:34]([C:31](=[NH:32])[NH2:33])[CH:35]=4)[C:40]=3[CH2:44][C:45](=[O:47])[NH2:46])=[O:26])=[CH:28][CH:29]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178478897HCID 178478897, compound

Product 1

HCID 178511920HCID 178511920, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 131721206HCID 131721206, compoundSolvent

Procedure

30 Milliliters of 20% hydrous pyridine was added to 1.71 g of 4-[(2-piperidinoethyl)aminoiminomethylamino]benzoic acid.dihydrochloride, 1.2 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.06 g of DCC and 52.4 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 4 days at room temperature. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of DMF, and the solution was added dropwise to a mixed liquid of 300 ml of acetone and 100 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-formic 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 2.1 ml of concentrated hydrochloric acid, and the solution was added dropwise to 450 ml of acetone, followed by stirring for 30 minutes under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.08 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom4 days
  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 DMF
  7. additionthe solution was added dropwise to a mixed liquid of 300 ml of acetone and 100 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 2.1 ml of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to 450 ml of acetone
  16. stirringby stirring for 30 minutes
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-8fb51115dbea4ecd8328abd225a85b66
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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