Pyridine → 6-Amidino-1-carbamoylmethyl-2-naphthyl 4-morpholinomethylbenzoate.dihydrochloride

HRID 1419222Notes

Reaction equation

HRID 1419222 reaction equation
N1C=CC=CC=1.[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1.[ClH:23].[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:23].[ClH:23].[O:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([O:20][C:32]3[CH:31]=[CH:30][C:29]4[C:34](=[CH:35][CH:36]=[C:27]([C:24](=[NH:25])[NH2:26])[CH:28]=4)[C:33]=3[CH2:37][C:38](=[O:40])[NH2:39])=[O:19])=[CH:16][CH:15]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 7035074-(morpholinomethyl)benzoic acidHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochloride

Product 1

HCID 701319946-Amidino-1-carbamoylmethyl-2-naphthyl 4-morpholinomethylbenzoate.dihydrochlorideYield 67.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

15 Milliliters of anhydrous pyridine was added to 612.2 mg of 4-morpholinomethylbenzoic acid, 703.9 mg of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 622.6 mg of DCC and 30.7 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 3 days under cooling with water. Thereafter, the same procedure as in Example 1 was carried out to obtain 440.7 mg of the desired product.

Workup

  1. temperatureunder cooling with ice

Sources & evidence

ORD record
ord-73405350c5924db0a431027c685d57d4
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

Loading…