Potassium Carbonate → HCID 178436368, compound

HRID 45962Notes

Reaction equation

HRID 45962 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].[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[S:25][CH:26]=[C:27]([CH2:28]Br)[C:23]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>>[CH2:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH2:28][C:27]2[C:23]3[CH:22]=[C:21]([Cl:20])[CH:31]=[CH:30][C:24]=3[S:25][CH:26]=2)[C:9]2[CH:17]=[CH:16][C:12]3[NH:13][CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 67443948N-(4-Ethylbenzyl)-1H-benzo[d]imidazol-5-amine

Product 1

HCID 178436368HCID 178436368, compound

Procedure

The compound was synthesized starting from N-(4-ethylbenzyl)benzimidazol-5-amine (251 mg; 1 mmol; 1 eq.), (5-chlorobenzo[b]-thiophen-3-yl)methylbromide (288 mg; 1.1 mmol; 1.1 eq.) and K2CO3 (152 mg; 1.1 mmol; 1.1 eq.) according to method 6; Yield: 0.125 g (29.0%); MS m/z: 432.6 [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); 4.85 (s, 2H); 6.79 (d, 1H, 4J=2.1 Hz); 6.84 (dd, 1H, 4J=2.1 Hz, 3J=8.9 Hz); 7.12-7.14 (m, 2H); 7.20-7.21 (m, 2H); 7.37 (d, 1H, 3J=8.9 Hz); 7.40 (dd, 1H, 4J=1.8 Hz, 3J=8.5 Hz); 7.47 (s, 1H); 7.93 (d, 1H, 4J=1.8 Hz); 7.94 (s, 1H); 8.00 (d, 1H, 3J=8.5 Hz); 12.18 (br s, 1H); HPLC (METHOD [A]): rt 19.69 min (100%)

Workup

  1. customThe compound was synthesized
  2. customrt 19.69 min (100%)

Sources & evidence

ORD record
ord-e934c6970ea34d5fada15bcc49485c2a
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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