Triethylamine → HCID 9827934, compound

HRID 1740895Notes

Reaction equation

HRID 1740895 reaction equation
Cl.Cl.[C:3]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]2[C:14]([CH2:15][CH2:16][NH:17][C:18]([C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]3)=[O:19])=[CH:13][N:12]=[CH:11]2)=[CH:7][CH:6]=1)#[N:4].CCN(CC)CC.[C:35]1([CH:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[BH3-]C#N.[Na+]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:14]([CH2:15][CH2:16][NH:17][C:18]([C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][N:21]3[CH2:42][CH:41]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:19])=[CH:13][N:12]=[CH:11]2)=[CH:26][CH:27]=1)#[N:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13696DiphenylacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86754663HCID 86754663, compound

Product 1

HCID 9827934HCID 9827934, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperidine-2(S)-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]-ethyl}-amide dihydrochloride (0.503 mmol) was dissolved in MeOH (3 mL) and the pH of the solution adjusted to 5 with Et3N. 2,2-Diphenylacetaldehyde (0.267 mL, 1.508 mmol) and NaCNBH3 (0.095 g, 1.508 mmol) were added, and the reaction mixture stirred for 18 hr at ambient temperature. The mixture was concentrated to remove the MeOH, then partitioned between CH2Cl2 and aq satd NaHCO3 solution. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to give the title compound after SiO2 chromatography eluting with CH2Cl2 : MeOH, NH4OH, 98:1.8:0., and conversion to the hydrochloride salt.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the MeOH
  3. custompartitioned between CH2Cl2
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-225c69bae5d042e0853337d132121acc
Source dataset
uspto-grants-1999_10
Patent number
US05972966

Reaction notes

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