Triethylamine → HCID 178483879, compound

HRID 452107Notes

Reaction equation

HRID 452107 reaction equation
FC(F)(F)C([O-])=O.C[Si](C#N)(C)C.[NH2:14][C:15]1[CH:23]=[CH:22][C:18]2[N:19]=[CH:20][NH:21][C:17]=2[CH:16]=1.CN(C)C[CH2:27][CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.[CH2:39]([N:41](CC)[CH2:42]C)C.[C:46](N1C=CN=C1)([N:48]1C=CN=[CH:49]1)=[O:47]>[Pd]>[CH3:39][N:41]([CH3:42])[CH2:27][CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C@@H:34]2[N:14]([C:15]3[CH:23]=[CH:22][C:18]4[NH:19][CH:20]=[N:21][C:17]=4[CH:16]=3)[C:46](=[O:47])[NH:48][CH2:49]2)=[CH:36][CH:37]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 84468TrifluoroacetateHCID 5469324-[3-(Dimethylamino)propoxy]benzaldehyde

Product 1

HCID 178483879HCID 178483879, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound was synthesized as trifluoroacetate salt starting from trimethyl silyl cyanide (1.88 mL, 20.72 mmol), 5-amino benzimidazole (0.82 g, 6.21 mmol), 4-(3-(dimethylamino)propoxy)benzaldehyde (1.0 g, 5.18 mmol), 10% Pd—C (250 mg), triethylamine (7.5 mL, 51.91 mmol), 1,1′-carbonyldiimidazole (1 g, 6.48 mmol). The product was further purified by prep HPLC using the following conditions: Column: Chiralpak AD-HMobile phase: Hexane: Ethanol (0.1% DEA); Flow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum and partitioned between water and chloroform. The separated organic layer was washed with brine solution. Dried over anhydrous sodium sulphate and concentrated in vacuum to afford 50 mg of the product as brown solid.

Workup

  1. customThe product was further purified by prep HPLC
  2. concentrationFlow rate: 32 mL/min, UV: 210 nm, Diluent: Mobile phase The prep fractions were concentrated in vacuum
  3. custompartitioned between water and chloroform
  4. washThe separated organic layer was washed with brine solution
  5. dry with materialDried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-36d4f660ed1b4c96ba06738695a4e4ca
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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