HCID 18792757, compound → HCID 53977211, compound

HRID 1004590Notes

Reaction equation

HRID 1004590 reaction equation
[F:1][C:2]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:7]([F:16])[CH:6]=[C:5]([N+:17]([O-])=O)[C:3]=1[NH2:4]>C(O)C.[Pd]>[F:16][C:7]1[C:8]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[C:2]([F:1])[C:3]([NH2:4])=[C:5]([NH2:17])[CH:6]=1

Participants

4

Reactant 1

HCID 18792757HCID 18792757, compound

Product 1

HCID 53977211HCID 53977211, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitroaniline derivative (10.0 g, 0.036 mol) (obtained in step 1 above) was hydrogenated using 10% Pd-C (2.0 g) in ethanol (40 mL), following an analogous procedure to that described in preparation 1 (step 4) to yield 4,6-difluoro-5-(4-methylpiperazin-1-yl)-1, 2-phenylenediamine (8.8 g, 98.7%) as a brown viscous oil, which was directly converted to 4,6-difluoro-5-(4-methylpiperazine-1-yl)-2-mercapto-1H-benzimidazole (6.7 g, 65%) by an analogous procedure to that described in preparation 1 (step 5) using carbon disulfide (5.5 g, 0.072 mol), potassium hydroxide (2.5 g, 0.043 mmol), ethanol (70 mL) and water (10 mL). mp 280-281° C.; IR (KBr) 3085, 1475 cm-1 ; 1H NMR (DMSO-d6) δd 2.22 (s, 3H, NCH3), 2.44 (m, 4H, N(CH2)2), 3.02 (m, 4H, N(CH2)2), 6.86 (d, J=12.8 Hz, 1H), 12.90 (brs, 1H, NH); Mass (m/z) 284 (M+.).

Workup

  1. customthat described in preparation 1 (step 4)

Sources & evidence

ORD record
ord-95951d1988b04a8d84a766fd8ec54dbe
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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