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

HRID 1004594Notes

Reaction equation

HRID 1004594 reaction equation
[F:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[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.[CH3:20][C:21]1[C:22]([CH2:33]Cl)=[N:23][CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]([F:32])([F:31])[F:30].[OH-].[Na+].[K+].[Br-]>C(O)C>[CH3:20][C:21]1[C:22]([CH2:33][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][N:15]([CH3:18])[CH2:14][CH2:13]4)=[CH:4][C:5]=3[N:9]=2)=[N:23][CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]([F:32])([F:30])[F:31]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 162176472-(Chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochlorideHCID 178480613HCID 178480613, compound

Product 1

HCID 187927622-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound (1.48 g, 64%) was prepared by the general procedure using 6-fluoro-5-(4-methylpiperazin-1-yl)-2-mercapto-1H-benzimidazole (1.33 g, 5.0 mmol) (obtained in preparation 4), 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride (1.5 g, 5.5 mmol), sodium hydroxide (0.4 g, 10.0 mmol) and ethanol (25 mL). mp 109-110° C.; IR (KBr) 3397, 1584, 1258 cm-1 ; 1H NMR (DMSO-d6) δ 2.38 (s, 3H, CH3), 2.80 (s, 3H, CH3), 3.12 (m, 4H, N(CH2)2), 3.40 (m, 4H, N(CH2)2), 4.48 (q, J=7.9 Hz, 2H, OCH2CF3), 4.60 (s, 2H, SCH2), 6.80 (d, J=5.8 Hz, 1H), 7.14 (d, J=7.1 Hz, 1H), 7.24 (d, J=11.7 Hz, 1H), 8.40 (d, J=5.5 Hz, 1H); Mass (m/z) 469 (M+).

Sources & evidence

ORD record
ord-721ea62bc8f34d64be55e78e028077f4
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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