Potassium Carbonate → HCID 178420843, compound

HRID 45950Notes

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:10]([CH2:20][C:19]2[CH:18]=[CH:17][C:16]([C:12]3[S:11][CH:15]=[CH:14][CH:13]=3)=[CH:23][CH:22]=2)[C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 136235-Aminobenzimidazole

HCID 27952532-[4-(bromomethyl)phenyl]thiophene

Product 1

HCID 178420843HCID 178420843, compound

Procedure

The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 4-(thiophen-2-yl)benzylbromide (557 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.09 g (18.9%); MS m/z: 478.4 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.70 (s, 4H); 6.73 (br s, 1H); 6.78 (dd, 1H, 4J=2.1 Hz, 3J=8.9 Hz); 7.10-7.11 (m, 2H); 7.33-7.36 (m, 5H); 7.45 (dd, 2H); 7.49 (dd, 2H); 7.59-7.60 (m, 4H); 7.91 (s, 1H); 11.99 (br s, 1H); HPLC (METHOD [A]): rt 19.76 min (100%)

Workup

customThe compound was synthesized
customrt 19.76 min (100%)

Sources & evidence

ORD record: ord-88a5293223a64e94b01792fd21bdd521
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541596B2

Reaction notes

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