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 1584271Notes

Reaction equation

HRID 1584271 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-955a4c06798a4e3d9c68f2ef4012b7f5
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

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