Potassium Carbonate → HCID 178436366, compound

HRID 45960Notes

Reaction equation

HRID 45960 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].[F:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([F:30])[C:28]=1[F:29])[CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>>[F:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([F:30])[C:28]=1[F:29])[CH2:24][N:8]([CH2:7][C:6]1[CH:18]=[CH:19][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[C:9]1[CH:17]=[CH:16][C:12]2[NH:13][CH:14]=[N:15][C:11]=2[CH:10]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27770623,4,5-Trifluorobenzyl bromideHCID 67443948N-(4-Ethylbenzyl)-1H-benzo[d]imidazol-5-amine

Product 1

HCID 178436366HCID 178436366, compound

Procedure

The compound was synthesized starting from N-(4-ethylbenzyl)benzimidazol-5-amine (251 mg; 1 mmol; 1 eq.), 3,4,5-trifluorobenzylbromide (248 mg; 1.1 mmol; 1.1 eq.) and K2CO3 (152 mg; 1.1 mmol; 1.1 eq.) according to method 6; Yield: 0.078 g (19.7%); MS m/z: 396.2 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 1.14 (t, 3H, 3J=7.6 Hz); 2.55 (q, 2H, 3J=7.6 Hz); 4.64 (s, 2H); 4.66 (s, 2H); 6.71-6.74 (m, 2H); 7.13-7.20 (m, 6H); 7.35 (d, 1H, 3J=8.2 Hz); 7.94 (s, 1H); 12.03 (br s, 1H); HPLC (METHOD [A]): rt 18.63 min (92.1%)

Workup

  1. customThe compound was synthesized
  2. customrt 18.63 min (92.1%)

Sources & evidence

ORD record
ord-9865d78d088445ff9c5b25725dc7b8ef
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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