Hydrochloric Acid → 5-[(5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carbonyl)-amino]-isophthalic Acid Dibenzyl Ester

HRID 1018309Notes

Reaction equation

HRID 1018309 reaction equation
[CH:1]1([CH2:8][C:9]2[NH:13][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)=[N:11][C:10]=2[C:24](O)=[O:25])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:27]([O:34][C:35](=[O:53])[C:36]1[CH:51]=[C:50]([NH2:52])[CH:49]=[C:38]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:42]([O:41][C:39](=[O:40])[C:38]1[CH:49]=[C:50]([NH:52][C:24]([C:10]2[N:11]=[C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[NH:13][C:9]=2[CH2:8][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)=[O:25])[CH:51]=[C:36]([C:35]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:53])[CH:37]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7023592Dibenzyl 5-aminoisophthalateHCID 115593315-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carboxylic Acid

Product 1

HCID 115784315-[(5-Cycloheptylmethyl-2-naphthalen-2-yl-1H-imidazole-4-carbonyl)-amino]-isophthalic Acid Dibenzyl EsterYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step c above (500 mg, 1.44 mmol) and 5-amino-isophthalic acid dibenzyl ester (520 mg, 1.44 mmol) in DMF (3 ml) was added 1-hydroxybenzotriazole (HOBt) (195 mg, 1.44 mmol), 4-dimethylaminopyridine (DMAP) (cat.) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (EDC) (280 mg, 1.44 mmol). The solution was kept at room temperature for 72 h, poured over 1M hydrochloric acid (20 ml) and the product was extracted with ethyl acetate (2×20 ml). The product crystallised from the ethyl acetate extracts. The crystals were collected by filtration, dried and triturated with methanol to afford a white solid (453 mg, 46%). 1H NMR (300 MHz, d6-DMSO) 13.00 (1H, br s), 10.50 (1H, s), 8.84 (2H, s), 8.61 (1H, s), 8.28 (2H, m), 8.00 (3H, m), 7.50 (12H, m), 5.41 (4H, s), 2.98 (2H, d), 2.00 (1H, m), 1.69-1.16 (12H, m).

Workup

  1. extractionthe product was extracted with ethyl acetate (2×20 ml)
  2. customThe product crystallised from the ethyl acetate
  3. filtrationThe crystals were collected by filtration
  4. customdried
  5. customtriturated with methanol

Sources & evidence

ORD record
ord-86b136cf8e21401ebff2bc04db296481
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

Loading…