Potassium Carbonate → HCID 178422721, compound

HRID 45954Notes

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

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 136235-Aminobenzimidazole

HCID 27954806-(Bromomethyl)-2-methylquinoline

Product 1

HCID 178422721HCID 178422721, compound

Procedure

The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), (2-methylquinolin-6-yl)methylbromide (519 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.067 g (15.1%); MS m/z: 444.5 [M+H]+, 222.8 [M+2H]2+; 1H-NMR (500 MHz, DMSO d6): δ 2.60 (s, 6H); 4.92 (s, 4H); 6.77-6.82 (m, 2H); 7.33-7.35 (m, 3H); 7.67 (dd, 2H, 4J=2.1 Hz, 3J=8.5 Hz); 7.77 (br s, 2H); 7.85-7.87 (m, 3H); 8.14 (d, 2H, 3J=8.5 Hz); 11.81 (br s, 1H); HPLC (METHOD [A]): doublepeak rt 6.61 min (61.2%), 6.84 min (38.8%)

Workup

customThe compound was synthesized
customdoublepeak rt 6.61 min (61.2%), 6.84 min (38.8%)

Sources & evidence

ORD record: ord-b342cd3636de42fbac290be08253a34f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541596B2

Reaction notes

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