Sodium Hydroxide → HCID 15454675, compound

HRID 1004593Notes

Reaction equation

HRID 1004593 reaction equation
[F:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:5]2[N:9]=[C:8]([SH:10])[NH:7][C:6]=2[CH:11]=1.Cl.[CH3:19][C:20]1[C:21]([CH2:26]Cl)=[N:22][CH:23]=[CH:24][CH:25]=1.[OH-].[Na+].[K+].[Br-]>C(O)C>[N:12]1([C:25]2[CH:24]=[CH:23][N:22]=[C:21]([CH2:26][S:10][C:8]3[NH:7][C:6]4[CH:11]=[C:2]([F:1])[C:3]([N:12]5[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]5)=[CH:4][C:5]=4[N:9]=3)[C:20]=2[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 130586832-(Chloromethyl)-3-methylpyridine hydrochlorideHCID 178505405HCID 178505405, compound

Product 1

HCID 15454675HCID 15454675, compoundYield 154.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound (0.95 g, 63%) was prepared by the general procedure using, 6-fluoro-5-(piperidin-1-yl)-2-mercapto-1H-benzimidazole (0.70 g, 2.8 mmol) (obtained in preparation 3), 4-(piperidin-1-yl)-3 )-methyl-2-chloromethylpyridine hydrochloride (0.91 g, 3.5 mmol), sodium hydroxide (0.30 g, , 7.7 mmol) and ethanol (15 mL). mp 161-162° C.; IR (KBr) 3430, 1581, 1429 cm-1 ; 1H NMR (CDCl3) δ 1.60 (m, 4H, 2×CH2), 1.74 (m, 8H, 2×(CH2)2), 2.30 (s, 3)H, CH3), 3.00 (m, 8H, 2×N(CH2)2), 4.32 (s, 2H, SCH2), 6.82 (d, J=5.4 Hz, 1H), 7.12 (d, J=7.7 Hz, 1H), 7.24 (d, J=12.1 Hz, 1H), 8.28 (d, J=5.5 Hz, 1H); Mass (m/z) 439 (M+).

Sources & evidence

ORD record
ord-894933d3454b46df8b5a612aae6466ef
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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