m-Chloroperbenzoic acid → 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazole

HRID 1004599Notes

Reaction equation

HRID 1004599 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:32])[C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].ClC1C=CC=C(C(OO)=[O:41])C=1.[K+].[Br-]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:32])[C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[CH:24][C:18]=3[N:17]=2)=[O:41])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 253877Potassium BromideHCID 187927622-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazole

Product 1

HCID 187927592-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazoleYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound (0.15 g, 51%) was prepared by the above general procedure using 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazole (0.28 g, 0.6 mmol) (obtained in example 20), m-chloroperbenzoic acid (50%, 0.25 g, 0.72 mmol) and chloroform (20 mL). mp 73-74° C.; IR (KBr) 3470, 1080 cm- 1; 1H NMR (CD3OD) δ 2.20 (s, 3H, CH3), 2.50 (s, 3H, CH3), 2.88 (t,J=4.6 Hz, 4H, N(CH2)2), 3.18 (t,J=4.8 Hz, 4H, N(CH2)2), 4.68 (q,J=8.2 Hz, 2H, OCH2CF3), 4.80 (s, 2H, SOCH2), 7.00 (d,J=5.8Hz, 1H), 7.24 (d,J=7.6Hz, 1H), 7.32 (d,J=12.2Hz, 1H), 8.18 (d,J=5.7Hz, 1H); Mass (m/z) 486 (M+ 1).

Sources & evidence

ORD record
ord-59a3b23fabaf49bc912c5c975543dfdf
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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