1,2-Dichloroethane → 2-(2,3-Dimethylbenzoyl)-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

HRID 1584271노트

반응식

HRID 1584271 반응식
Cl.[C:2]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH2:15][NH:16][C:17]([C@@H:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][NH:20]3)=[O:18])=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3].ON1C2C=CC=CC=2N=N1.C(Cl)CCl.[CH3:45][C:46]1[C:54]([CH3:55])=[CH:53][CH:52]=[CH:51][C:47]=1[C:48](O)=[O:49].CN1CCOCC1>CN(C=O)C>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH2:15][NH:16][C:17]([C@@H:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][N:20]3[C:48](=[O:49])[C:47]3[CH:51]=[CH:52][CH:53]=[C:54]([CH3:55])[C:46]=3[CH3:45])=[O:18])=[CH:12][N:11]=[CH:10]2)=[CH:29][CH:30]=1)#[N:3]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 701220621,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride

생성물 1

HCID 154109502-(2,3-Dimethylbenzoyl)-1,2,3,4-tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride (Example 1, Step C) (0.23 g, 0.52 mmol) in DMF (5 mL) was added l-hydroxybenzotriazole (0.079 g, 0.52 mmol), EDC (0.099 g, 0.52 mmol), 2,3-dimethylbenzoic acid (0.077 g, 0.52 mmol) and N-methylmorpholine (0.23 mL, 2.08 mmol). After stiffing for 18 hr. the mixture was evaporated in vacuo and the residue was partitioned betweem EtOAc (50 mL) and saturated NaHCO3 solution (30 mL). The organic layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration and concentration gave the title compound after purification by preparative HPLC on a Delta-pak C-18 column eluting with 0.1%TFA/H2O: 0.1%TFA/CH4CN, 95:5 to 5:95.

후처리

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was partitioned betweem EtOAc (50 mL) and saturated NaHCO3 solution (30 mL)
  3. washThe organic layer was washed with saturated NaCl solution (30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-955a4c06798a4e3d9c68f2ef4012b7f5
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932590

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