Pyridine → 6-amidino-1-carbamoylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate.dihydrochloride

HRID 1419213Notes

Reaction equation

HRID 1419213 reaction equation
N1C=CC=CC=1.[ClH:7].[NH: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].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O>[ClH:7].[ClH:7].[NH:10]1[CH2:11][CH2:12][N:8]=[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 10868Dicyclohexylcarbodiimide2×HCID 688307174-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoic acid.hydrochlorideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochloride

Product 1

HCID 701369326-amidino-1-carbamoylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate.dihydrochloride

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 962WaterSolvent

Procedure

45 Milliliters of 20% hydrous pyridine was added to 2.85 g of 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoic acid.hydrochloride, 3 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 2.65 g of N,N'-dicyclohexylcarbodiimide (hereinafter referred to as "DCC") and 131 mg of 4-dimethylaminopyridine (hereinafter referred to as "DMAP"), followed by stirring for 2 hours under cooling with ice and 3 days under cooling with water. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of N,N-dimethylformamide (hereinafter referred to as "DMF"), and a small amount of the insoluble matter was filtered off. The filtrate was added dropwise to 500 ml of a mixed liquid of ether and acetone (10:1) and this was stirred for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product.

Workup

  1. temperatureunder cooling with ice and 3 days
  2. filtrationThe precipitate was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added 15 ml of N,N-dimethylformamide (
  5. filtrationwas filtered off
  6. additionThe filtrate was added dropwise to 500 ml of a mixed liquid of ether and acetone (10:1)
  7. stirringthis was stirred for 24 hours
  8. temperatureunder cooling with ice
  9. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-82641fbda90a442d9256e5646950bfa9
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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