1-[2-(Morpholin-4-ylmethyl)phenyl]methanamine

General procedure: Additional amide analogs were prepared by adding 1.5 equivalents of an amine which will provide the desired substituents into a 1 dram vial (1.5 eq.) along with lithium 5-amino-7- methoxyimidazo[1, 2-c]quinazoline-2-carboxylate (30 mg, 0.114 mmol) and a DMF solution (1.0 ml) solution of DIPEA (0.079 ml, 0.454 mmol), shaking the vial for 5 minutes in a Bohdan Miniblock Shaker and then adding 1-propanephosphonic acid cyclic anhydride (50% w/w in EtOAc, 64.7 mul, 0.109 mmol), and continuing to shake the vial at RT overnight. The completed reaction was quenched with 1.0 ml water and the organic layer separated by filtering through a Varian 2 ml Reservior Frit and a Whatman 0.45mum syringe filter to remove emulsion, followed by solvent removal using a Genevac. The crude residue was dissolved in 1.0 ml DMSO and purified by LC/MS.General procedure: A solution of carboxylic acid (0.5 mmol) and HATU (0.55 mmol)in anhydrous DMF (2 mL) was stirred at ambient temperature for10 min. To this solution, DIPEA (0.6 mmol) and correspondingamine (0.54 mmol) were added successively and the mixture wasstirred for 18 h. After concentration under reduced pressure, thereaction mixture was treated with water (5 mL) and extracted withDCM (2 5 mL). After evaporation of the solvent, the residue wascrystallized from an appropriate solvent or subjected to columnchromatography on silica gel (DCM/MeOH) or preparative HPLCGeneral procedure: To a microwave vial containing a solution of Boc-L-glutamic acid tert-butyl ester (0.165 mmol, 1.0 equiv) and HATU (0.165 mmol, 1.0 equiv) in DMF (1.65 mL) was added the amine followed by DIPEA (57.5 muL, 2.0 equiv). The vial was sealed and heated under microwave irradiation for 30 min at 120 C. Upon completion, the reaction was partitioned between water and CH2Cl2, extracted 3× with CH2Cl2, dried over anhydrous Na2SO4, and concentrated under vacuum. Compounds were purified via reverse phase chromatography (5-95% acetonitrile/water) to afford the N-Boc-glutamylanilide-tert-butyl esters. The compounds were transferred to vials followed by the addition of 2.0 mL of 4.0 M HCl in dioxane. The reaction stirred at 40 C for 4 h. The reactions were concentrated under vacuum to afford the title compounds which were used without further purification.General procedure: To a solution containing S.I.-1 (0.20 g, 0.81 mmol) in 2 mL EtOH in a microwave reaction vial which could be sealed with a Teflon cap was added 4-amino-2, 2, 6, 6-tetramethylpiperidine (0.13 g, 0.81 mmol). The tube was briefly flushed with an Argon stream (approximately 30 s) and sealed. The reaction was heated to 150 C for 1 hr in microwave and then allowed to cool to room temperature and stand for 12 hours, during which time a glassy solid formed. The solid was collected by filtration, washed with cold hexanes, and dried to give 140 mg (48%) of the product as a colorless crystalline solid.c) methyl [(4E)-1-(2-chloro-4-fluorophenyl)-4-(2-methoxy-1-{[2-(morpholin-4-yl methyl)benzyl]amino}ethylidene)-5-oxo-4, 5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII), Scheme 2).; [Show Image] The mixture of the above obtained methyl [1-(2-chloro-4-fluorophenyl)-5-hydroxy-4-(methoxyacetyl)-1H-pyrazol-3-yl]acetate (Compound of Formula (X), 400mg, 1.12mmol, leq), and Example 92: 4-Chloro-6-(2-morpholin-4-ylmethyI-benzyIamino)-2H-phthalazin-l- one; A mixture 6-bromo-4-chloro-2H-phthalazin-l-one (150 mg, 0.58 mmol), 2- mophiholin-4-ylmethyl-benzylamine (132 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058

Molecular Weight:206.28
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:206.141913202
Monoisotopic Mass:206.141913202
Topological Polar Surface Area:38.5
Heavy Atom Count:15
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes