Triethylamine → HCID 178494852, compound

HRID 452103Notes

Reaction equation

HRID 452103 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.C[Si](C#N)(C)C.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]2[N:25]=[CH:26][NH:27][C:23]=2[CH:22]=1.C(N(CC)CC)C.[C:37](N1C=CN=C1)([N:39]1C=CN=[CH:40]1)=[O:38]>[Pd]>[NH:25]1[C:24]2[CH:28]=[CH:29][C:21]([N:20]3[CH:10]([C:9]4[CH:12]=[CH:13][C:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=4)[CH2:40][NH:39][C:37]3=[O:38])=[CH:22][C:23]=2[N:27]=[CH:26]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 136235-AminobenzimidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 57488479HCID 57488479, compound

Product 1

HCID 178494852HCID 178494852, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound was synthesized according to method 2 starting from 4-(3-methoxypropyl)benzaldehyde (1.5 g, 8.42 mmol), trimethyl silylcyanide (1.6 mL, 16.84 mmol), 5-amino benzimidazole (1.23 g, 9.26 mmol), 10% Pd—C (300 mg), triethylamine (5.8 mL, 41.97 mmol), 1,1′-carbonyldiimidazole (0.84 g, 5.24 mmol). Yield: 0.055 g (0.6%); MS m/z 293.4 (M+H)+; 1H NMR (DMSO, 400 MHz): δ 2.21 (s, 3H); 3.05-3.09 (m, H); 3.83-3.87 (m, H); 5.49-5.53 (m, H); 7.01-7.10 (m, 2H); 7.15 (d, H, J=7.9 Hz); 7.19 (s, H); 7.52-7.55 (m, H), 7.60 (d, H, J=8.7 Hz); 7.84 (s, H); 9.16 (s, H), HPLC (λ=214 nm, [B]: rt 8.05 min (100%).

Workup

  1. customThe compound was synthesized
  2. customrt 8.05 min (100%)

Sources & evidence

ORD record
ord-edf18f1438bf44ceb8b655667cfd14a8
Source dataset
uspto-grants-2013_07
Patent number
US08486940B2

Reaction notes

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