2-Amino-3-methylbenzamide

2-Amino-3-methylbenzoic acid (2.93 g, 19.8 mmol) in dry DMF (78 mL) was treated with 1, 1-carbonyl-diimidazole (3.14 g, 19.4 mmol) at 70°C under Ar for lh, after which aq. NHStep A: To 2-amino-3-methylbenzoic acid (1.5 g, 10 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (2.0 g, 13 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.3 g, 12 mmol), ammonium chloride (2.3 g, 42 mmol), and diisopropylethylamine (7.5 ml, 42 mmol). The mixture was purged with N1161) A 500 mL round bottom flask was charged with 2-amino-3-methylbenzoic acid (Combi-Blocks, 4.0 g, 26.5 mmol, 1 eq), NH00373] Step A: To solution of 2-amino-3-methylbenzoic acid (4.0 g, 26.5 mmol) in degassed DMF (40 mL) were added HOBt (4.28 g, 31.7 mmol), DIEA (5.52 mL, 31.7 mmol), and 2N NHAccordingtoaliteratureprocedure, 3toasolutionof2-amino-3-methylbenzoicacid(151mg, 1.00mmol, 1.0eq)indegassedDMF(2.00mL)wereaddedHOBt(162mg, 1.20mmol, 1.2eq.), EDCI.HCl(230mg, 1.20mmol, 1.2eq.), N, N-diisopropylethylamine(350μL, 2.00mmol, 2.0eq), and7MNH3/MeOH(429μL, 1.50mmol, 1.5eq.).Thesolutionwasstirredatroomtemperaturefor24hoursthenpouredoverwaterandtheaqueouslayerextractedwithEtOAc(320mL), thecombinedorganiclayerswashedwithbrine(25mL), driedwithNa2SO4andconcentratedinvacuo.TheresiduewaspurifiedbyFCC(gradient50percentEtOAc/hexanes to 80percent EtOAc/hexanes) to give 2-amino-3-methylbenzamide (90.0 mg, 0.599mmol, 60percent)asawhiteamorphoussolid;mp:144–146°C, lit.144–145°C.To a stirred solution of 2-amino-3-methyl-benzoic acid (0.5 g, 3.31 mmol) in THF (15 mL), EDC.HCl (0.948 g, 4.97 mmol), HOBt·NH3 (0.745 g, 4.97 mmol) and DIPEA (1.76 mL, 9.93mmol) were added at RT and stirred for 6 h (TLC indicates complete conversion of startingmaterial). The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3x 100 mL). The combined organic extracts were washed with water (2 x 50 mL), brine (40mL), dried over Na2S04 and concentrated under reduced pressure to give the crude residue The crude material was purified by column chromatography (100-200 silica gel, 20 g, 50percentEtOAc-Hexane) to afford 2-amino-3-methyl-benzamide (0.3 g, 60percent) as a white solid.LCMS: m/z: 151.09 [M+H] +.Step A:

Molecular Weight:150.18
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.079312947
Monoisotopic Mass:150.079312947
Topological Polar Surface Area:69.1
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes