Pyridine → HCID 70132975, compound

HRID 1419242Notes

Reaction equation

HRID 1419242 reaction equation
N1C=CC=CC=1.[ClH:7].[S:8]1[CH2:12][CH2:11][N:10]=[C:9]1[NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.Cl.[C:24]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([CH2:37][C:38](=[O:40])[NH2:39])=[C:32](O)[CH:31]=[CH:30]2)(=[NH:26])[NH2:25].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].[S:8]1[CH2:12][CH2:11][N:10]=[C:9]1[NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][C:32]2[CH:31]=[CH:30][C:29]3[C:34](=[CH:35][CH:36]=[C:27]([C:24](=[NH:25])[NH2:26])[CH:28]=3)[C:33]=2[CH2:37][C:38](=[O:40])[NH2:39])=[O:19])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 70132939HCID 70132939, compoundHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochloride

Product 1

HCID 70132975HCID 70132975, compoundYield 43.2%

Reagents, catalysts & solvents 2

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

Procedure

15 Milliliters of 20% hydrous pyridine was added to 1.5 g of 4-[(4,5-dihydrothiazol-2-yl)amino]benzoic acid.hydrochloride, 1.62 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 1.43 g of DCC and 70.8 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. Then, the precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 20 ml of DMF, and the resulting solution was added dropwise to a mixed liquid of 200 ml of acetone and 200 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 10 ml of methanol and 0.97 ml of concentrated hydrochloric acid, and the solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 651 mg of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. custom24 hours
  3. customat room temperature
  4. filtrationThen, the precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 20 ml of DMF
  7. additionthe resulting solution was added dropwise to a mixed liquid of 200 ml of acetone and 200 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 10 ml of methanol and 0.97 ml of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether
  16. stirringby stirring for 24 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-3f7aec2207744e7daa81cba2d6c3f26a
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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