Sodium Hydroxide → 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazole

HRID 1004592Notes

Reaction equation

HRID 1004592 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]([CH2:32]Cl)=[N:22][CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]([F:31])([F:30])[F:29].[OH-].[Na+]>C(O)C>[CH3:19][C:20]1[C:21]([CH2:32][S:10][C:8]2[NH:7][C:6]3[CH:11]=[C:2]([F:1])[C:3]([N:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)=[CH:4][C:5]=3[N:9]=2)=[N:22][CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]([F:31])([F:29])[F:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 162176472-(Chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochlorideHCID 178505405HCID 178505405, compound

Product 1

HCID 187927512-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazoleYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound (0.45 g, 50%) was prepared by the general procedure using 6-fluoro-5-(piperidin-1-yl)-2-mercapto-1H-benzimidazole (0.5 g, 2.0 mmol) (obtained in preparation 3), 3-methyl-4-(2,2,2,-trifluoroethoxy)-2-chloromethylpyridine hydrochloride (0.47 g, 2.0 mmol), sodium hydroxide (0.16 g, 4.0 mmol) and ethanol (10 mL). mp 160-161° C.; 1R (KBr) 3122, 1585, 1432 cm-1 ; 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.80 (m, 4H, (CH2)2), 2.38 (s, 3H, CH3), 3.00 (m, 4H, N(CH2)2), 4.40 (s, 2H, SCH2), 4.46 (q, J=7.8 Hz, 2H, OCH2CF3), 6.74 (d, J=5.5 Hz, 1H), 7.18 (d, J=7.6 Hz, 1H), 7.26 (d, J=10.0 Hz, 1H), 8.42 (d, J=5.5 Hz, 1H), 12.50 (s, 1H, NH); Mass (m/z) 454 (M+).

Sources & evidence

ORD record
ord-155555fe27c2413abaab626f18434be1
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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