Sodium Hydroxide → HCID 18792772, compound

HRID 1004595Notes

Reaction equation

HRID 1004595 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]([CH2:27]Cl)=[N:23][CH:24]=[CH:25][CH:26]=1.[OH-].[Na+]>C(O)C>[CH3:20][C:21]1[C:22]([CH2:27][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][CH:26]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 130586832-(Chloromethyl)-3-methylpyridine hydrochlorideHCID 178480613HCID 178480613, compound

Product 1

HCID 18792772HCID 18792772, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound (0.6 g, 22%) was prepared by the general procedure using 6-fluoro-5-(4-methylpiperazin-1-yl)-2-mercapto-1H-benzimidazole (2.0 g, 7.5 mmol) (obtained in preparation 4), 3-methyl-2-chloromethylpyridine hydrochloride (1.0 g, 7.5 mmol), sodium hydroxide (0.36 g, 9.0 mmol) and ethanol (15 mL). IR (Neat) 3150, 1429 cm-1 ; 1H NMR (CDCl3) δ 2.42 (s, 3H, CH3), 2.50 (s, 3H, CH3), 2.90 (m, 4H, N(CH2)2), 3.20 (m, 4H, N(CH2)2), 4.38 (s, 2H, SCH2), 7.12 (d, J=7.6 Hz, 1H), 7.20-7.26 (m, 2H), 7.58 (d, J=7.4 Hz, 1H), 8.46 (d, J=4.6 Hz, 1H); Mass (m/z) 371 (M+.).

Sources & evidence

ORD record
ord-a62396d7dd734b9ba55a4e8041d44b67
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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