1,2-Dichloroethane → 3-[[2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxobutyl)-2-oxo-1,3,4-benzotriazepin-3-yl]acetyl]amino]-N-methylsulfonylbenzamide

HRID 2113312노트

반응식

HRID 2113312 반응식
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[CH:6]1([C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:15](=[O:30])[N:14]([CH2:31][C:32]([NH:34][C:35]3[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=3)[C:38](O)=[O:39])=[O:33])[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:6]1([C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:15](=[O:30])[N:14]([CH2:31][C:32]([NH:34][C:35]3[CH:43]=[CH:42][CH:41]=[C:37]([C:38]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:39])[CH:36]=3)=[O:33])[N:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 72879MethanesulfonamideHCID 115277383-{2-[5-Cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic Acid

생성물 1

HCID 167330513-[[2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxobutyl)-2-oxo-1,3,4-benzotriazepin-3-yl]acetyl]amino]-N-methylsulfonylbenzamide수율 83%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Methanesulfonamide (96 mg, 1.00 mmol) was added to a solution of 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic acid (Example 2)(409 mg, 0.80 mmol), EDC (207 mg, 1.08 mmol) and DMAP (122 mg, 1.00 mmol) in DCM (20 ml) at room temperature. After stirring for 17 h, the mixture was washed with 5% KHSO4 (50 ml), brine (50 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by flash column chromatography (MeOH-DCM (1:10) to afford the title compound as a white crystalline solid (392 mg, 83%). 1H NMR (DMSO-d6) 9.99 (1H, s), 8.02 (1H, s), 7.63-7.36 (5H, m), 7.23 (1H, t), 7.13 (1H, d), 4.73 (2H, dd), 4.29 and 4.25 (2H, d×2), 3.24 (3H, s), 2.87 (1H, m), 1.80-1.48 (6H, m), 1.30-1.09 (13H, m). The compound was further characterised as the N-methyl-D-glucamine salt. Found: C, 53.93; H, 7.07; N, 10.17%; C30H37N5O6S.C7H17NO5.2.0H2O requires: C, 53.74; H, 7.07; N, 10.16%.

후처리

  1. washthe mixture was washed with 5% KHSO4 (50 ml), brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and evaporation of the solvent
  4. customgave the crude product which
  5. customwas purified by flash column chromatography (MeOH-DCM (1:10)

출처 및 근거

ORD 기록
ord-3f1b051071ef40619d2222c2afa3eb65
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524837B2

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