Potassium Carbonate → HCID 178436364, compound

HRID 45961Notes

Reaction equation

HRID 45961 reaction equation
[CH2:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][C:12]3[N:13]=[CH:14][NH:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)#[N:21].C([O-])([O-])=O.[K+].[K+]>>[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:8]([CH2:7][C:6]2[CH:18]=[CH:19][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:9]2[CH:17]=[CH:16][C:12]3[NH:13][CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:24][CH:23]=1)#[N:21]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 67443948N-(4-Ethylbenzyl)-1H-benzo[d]imidazol-5-amine

Product 1

HCID 178436364HCID 178436364, compound

Procedure

The compound was synthesized starting from N-(4-ethylbenzyl)benzimidazol-5-amine (251 mg; 1 mmol; 1 eq.), 4-cyanobenzylbromide (216 mg; 1.1 mmol; 1.1 eq.) and K2CO3 (152 mg; 1.1 mmol; 1.1 eq.) according to method 6; Yield: 0.127 g (34.7%); MS m/z: 367.2 [M+H]+; 1H-NMR (500 MHz, DMSO d6): (Rotamers) δ 1.14 (t, 3H, 3J=7.6 Hz); 2.55 (q, 2H, 3J=7.6 Hz); 4.63 (s, 0.7H); 4.66 (s, 1.3H); 4.72 (s, 0.7H); 4.76 (s, 1.3H); 6.61 (br s, 0.7H); 6.67-6.68 (m, 0.7H); 6.75-6.77 (m, 0.3H); 6.81 (br s, 0.3H); 7.14 (d, 2H, 3J=7.9 Hz); 7.19 (d, 2H, 3J=7.9 Hz); 7.25-7.27 (m, 0.3H); 7.36 (d, 0.7H, 3J=8.9 Hz); 7.46 (d, 2H, 3J=8.2 Hz); 7.77 (d, 2H, 3J=8.2 Hz); 7.87 (s, 0.7H); 7.97 (s, 0.3H); 11.85 (s, 0.7H); 12.04 (s, 0.3H); HPLC (METHOD [A]): rt 17.49 min (98.4%)

Workup

  1. customThe compound was synthesized
  2. customrt 17.49 min (98.4%)

Sources & evidence

ORD record
ord-1b672dc8dd904266bd394f91f14d23a4
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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