Pyridine → 6-amidino-1-carbamoylmethyl-2-naphthyl 3-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate.dihydrochloride

HRID 1419220Notes

Reaction equation

HRID 1419220 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:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18].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.O>[ClH:7].[ClH:7].[NH:10]1[CH2:11][CH2:12][N:8]=[C:9]1[NH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([O:19][C:32]1[CH:31]=[CH:30][C:29]2[C:34](=[CH:35][CH:36]=[C:27]([C:24](=[NH:25])[NH2:26])[CH:28]=2)[C:33]=1[CH2:37][C:38](=[O:40])[NH2:39])=[O:18]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 701303823-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoic acid.hydrochlorideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochloride

Product 1

HCID 701303896-amidino-1-carbamoylmethyl-2-naphthyl 3-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate.dihydrochlorideYield 66.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

15 Milliliters of 20% hydrous pyridine was added to 634.1 mg of 3-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoic acid.hydrochloride, 676.7 mg of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 598 mg of DCC and 29.5 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours under cooling with water. Thereafter, the same procedure as in Example 1 was carried out to obtain 439.5 mg of the desired product.

Workup

  1. temperatureunder cooling with ice

Sources & evidence

ORD record
ord-d6d7a4c1eecd4a65921669bff4d5ecec
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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