Formaldehyde → 4-[5-(5-Chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-(2-dimethylamino-ethoxy)-benzonitrile

HRID 1421735Notes

Reaction equation

HRID 1421735 reaction equation
N[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[C:11]([CH2:13][N:14]2[C:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]4=[O:33])=[N:24][CH:25]=3)=[CH:17][N:16]=[CH:15]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[CH2:34]=O.[BH3-][C:37]#[N:38].[Na+].[OH-].[Na+]>C1COCC1>[Cl:32][C:30]1[CH:29]=[CH:28][C:27](=[O:33])[N:26]([C:23]2[CH:22]=[CH:21][C:20]([CH2:19][C:18]3[N:14]([CH2:13][C:11]4[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:4][CH2:3][CH2:2][N:38]([CH3:37])[CH3:34])[CH:12]=4)[CH:15]=[N:16][CH:17]=3)=[CH:25][N:24]=2)[CH:31]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 187797582-(2-Amino-ethoxy)-4-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

Product 1

HCID 187797034-[5-(5-Chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-(2-dimethylamino-ethoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Amino-ethoxy)-4-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile (L-824,459, 43 mg, 0.09 mmol) was dissolved in THF (1 mL) and CH2O (37% wt. in H2O, 14 μl, 0.18 mmol) was added. The solution was treated with NaCNBH3 (11.7 mg, 0.18 mmol) and the reaction mixture stirred at room temperature for 2 hours. 10% aqueous NaOH was added to the mixture and extracted with CH2Cl2. The water layer was extracted with CH2Cl2 (2×10 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated. Flash chromatography [8% MeOH(NH4OH 5%)/CH2Cl2 ] yielded the final product.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe water layer was extracted with CH2Cl2 (2×10 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a77f37f6e1a477094289513b30c986a
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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