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

HRID 1584270Notes

Reaction equation

HRID 1584270 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].CCN(CC)CC.[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C([BH3-])#N.[Na+]>CO>[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[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:18])=[CH:12][N:11]=[CH:10]2)=[CH:29][CH:30]=1)#[N:3]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 701220621,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride

Product 1

HCID 154109492-Benzyl-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 887MethanolSolvent

Procedure

1,2,3,4-Tetrahydro-isoquinoline-3(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide hydrochloride (0.15 g, 0.33 mmol) was dissolved in MeOH (7 mL). Et3N was added to this solution dropwise until the pH=5. To the solution was added benzaldehyde (0.069 mL, 0.65 mmol) and sodium cyanoborohydride (0.041 g, 0.65 mmol). After stirring for 18 hr. the mixture was evaporated in vacuo and the residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (30 mL). The organic layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration and concentration to dryness gave the title compound after purification on silica gel eluting with CH2Cl2 :

Workup

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

Sources & evidence

ORD record
ord-6e4e5af36b64422fbe13a26b6ed0ca6e
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

Loading…