Benzaldehyde → HCID 178517951, compound

HRID 452087Notes

Reaction equation

HRID 452087 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Si]([C:23]#[N:24])(C)(C)C.C([O:32][CH2:33]C)(OCC)OCC.[BH4-].[Na+]>Cl>[NH:6]1[C:5]2[CH:9]=[CH:10][C:2]([N:1]3[CH:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:33](=[O:32])[NH:24][CH2:23]3)=[CH:3][C:4]=2[N:8]=[CH:7]1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 136235-AminobenzimidazoleHCID 31214Ethyl orthoformateHCID 82115Trimethylsilyl cyanideHCID 4311764Sodium borohydride

Product 1

HCID 178517951HCID 178517951, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The compound was synthesized starting from 5-aminobenzimidazole (0.75 g, 5.61 mmol), benzaldehyde (0.52 mL, 5.1 mmol), TMSCN (0.64 mL, 5.1 mmol), conc. aqueous HCl (10 mL), triethyl orthoformate (13 mL, excess), NaBH4 (0.227 g, 6 mmol) as described in method 4. Yield: 0.088 g (6.2%); MS m/z 279.3 (M+H)+; 1H NMR (400 MHz, DMSO-D6): δ 4.78-4.80 (m, H); 5.04-5.05 (m, H); 5.17-5.19 (m, H); 6.23 (d, H, J=2.1 Hz); 6.79 (dd, H, 3J=9.1 Hz, 4J=2.1 Hz); 7.24-7.27 (m, H); 7.30-7.36 (m, 4H); 7.59 (d, H, J=9.1 Hz); 8.89 (s, H); 9.16 (s, H), HPLC (λ=214 nm), [B]: rt 6.43 min (97.8%).

Workup

  1. customThe compound was synthesized
  2. customrt 6.43 min (97.8%)

Sources & evidence

ORD record
ord-73345e2b7bbe4cfe91eaef0edb68f137
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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