5-BROMO-3-METHYL-BENZENE-1,2-DIAMINE

N4 -(5-Cyclopropyl-lH-pyrazol-3-yl)- N2 -((7-methyl-lH-benzo[d]imidazol-5-yl)methyl)-pyrimidine-2, 4- diamine (1-26) step 1 : To a suspension of 4-bromo-2-methyl-6-nitroaniline (2.0 g, 8.7 mmol) in EtOH (20 mL) was added SnC^ (5.0 g, 26.1 mmol). The reaction mixture was heated at reflux for 14 h, cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc (100 mL) and partitioned between satd. aq. NaHC03 solution (200 mL). The resulting slurry was filtered through a pad of Celite® and the wet cake was washed with EtOAc (3 x 50 mL). The filtrate was washed sequentially with satd. aq. NaHC03, water, and brine, dried (MgS04), filtered and concentrated in vacuo to afford 1.27 g (72percent) of 5-bromo-3- methylbenzene-l, 2-diamine (72) as yellow oil: MS (ESI) m/z = 201.1 [M+l] +.5-Bromo-3-methyl-benzene-1, 2-diamine: To a suspension of 4-bromo-2-methyl-6-nitro-phenylamine (20 g, 0.086 mol) in ethanol (200 mL) was added tin chloride dihydrate (49.2 g, 0.258 mol). The reaction mixture was heated to reflux for 14 h, cooled to room temperature, and concentrated in vacuo. The residue was diluted with ethyl acetate (150 mL) and treated with triethylamine (40 mL). The resulting slurry was filtered through a pad of celite, and the filtercake was rinsed with three portions ethyl acetate (50 mL). The filtrate was washed with saturated NaHCO3, water, and brine, then dried over Na2SO4 and filtered. After removal of the solvent, the residue was purified by flash chromatography on silica gel (30percent EtOAc/hexane, then 5percent MeOH/CH2Cl2) to yield the title compound (10.26 g, 59percent) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 6.77 (1H, d, J=2.0 Hz), 6.74 (1H, d, J=2.0 Hz), 2.16 (3H, s). LCMS (M+H)+ m/z 201. (t=0.83 min.).Example 4 1- (2-Cyclopropyl-l, 4-dimethyl-lH-benzimidazol-6-yl ) -4- ( (4- fluorobenzyl) oxy) pyridin-2 ( 1H) -one A) 5-Bromo-3-methylbenzene-l, 2-diamine To a stirred solution of compound 4-bromo-2-methyl-6- nitroaniline (5.0 g) in EtOH (85 ml) and water (43 ml) were added iron powder (6.0 g) and CaCl

Molecular Weight:201.06
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:199.99491
Monoisotopic Mass:199.99491
Topological Polar Surface Area:52
Heavy Atom Count:10
Complexity:118
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes