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

HRID 1018309

반응식

HRID 1018309 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-86b136cf8e21401ebff2bc04db296481
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479531B1

연결된 노트

불러오는 중…