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Chemical Structure| 1419957-49-5
Chemical Structure| 1419957-49-5
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CAS No. :1419957-49-5 MDL No. :MFCD27991612
Formula : C15H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 277.32 Pubchem ID :-
Synonyms :

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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1419957-49-5 ]

[ 1419957-49-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 1419957-49-5 ]
  • [ 1419954-10-1 ]
  • [ 1419949-20-4 ]
YieldReaction ConditionsOperation in experiment
24%
Stage #1: With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 20℃;
Example 5: N-Cyclopropylmethyl-2-[4-(4-methoxy-benzoyl)-piperidin-1-yl]-N-(4-oxo- -tetrahydro-4H-pyrano[4, 3-d]pyrimidin-2-ylmethyl)-acetamideTo a solution of [4-(4-methoxy-benzoyl)-piperidin-1-yl]-acetic acid (0.071 g, 0.26 mmol, 1 eq.) and DIEA (0.089 mL, 0.51 mmol, 2 eq.) in 2 mL of DMF was added HATU (0.107 g, 0.281 mmol, 1.1 eq.). The resulting mixture was stirred at room temperature for 30 min. 2-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (0.06 g, 0.26 mmol, 1 eq.) in 1 mL of DMF was added and the mixture was stirred at room temperature overnight. After 18 h, the reaction mixture was diluted with H20 (10 mL) and extracted with dichloromethane (3 x 50 mL). The combined organics were concentrated and purified by preparative HPLC (20-100percent CH3CN/H20 over 10 min with 0.1 percent TFA, sun fire C18 OBD 50x50 mm column with flow rate of 60 mL/min) to give the title compound as a white solid (0.03 g, 24percent). 1H NMR (400 MHz, MeOD) δ ppm 7.94 - 8.07 (m, 2 H), 6.98 - 7.10 (m, 2 H), 4.64 - 4.70 (m, 1 H), 4.54 - 4.60 (m, 1 H), 4.44 - 4.52 (m, 2 H), 4.28 - 4.37 (m, 1 H), 3.94 - 3.99 (m, 1 H), 3.91 - 3.95 (m, 2 H), 3.88 (s, 3 H), 3.67 - 3.80 (m, 2 H), 3.40 - 3.61 (m, 1 H), 3.33 - 3.40 (m, 2 H), 3.09 - 3.27 (m, 2 H), 2.50 - 2.72 (m, 2 H), 1 .92 - 2.26 (m, 4 H), 0.83 - 1 .15 (m, 1 H), 0.12 - 0.67 (m, 4 H). HRMS calculated for C27H35N405 495.2607, found (ESI, [M + H]+) 495.2606. MS (ESI) m/z 495.3 (M+H)+. Retention time: 2.89 min (5-95percent CH3CN/H20 over 7.75 min with 0.1 percent formic acid, Inertsil ODS3 100x3 mm C18 column with flow rate of 1.0 mL/min).Alternate procedure 1To a well stirred suspension of 2-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro- pyrano[4,3-d]pyrimidin-4-one (15.66 g, 57.6 mmol) in dichloromethane (600 mL) was added 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (16.45 g, 59.3 mmol), followed by triethylamine (24 mL, 173 mmol), 1 H-benzo[d][1 ,2,3]triazol-1 -ol hydrate (21 .41 g, 140 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1 ,3-diamine hydrochloride (13.26 g, 69.2 mmol). The resulting yellow suspension was stirred for 12 h, filtered and then washed with water three times (250 mL, 150 mL, then 50 mL). The organic layer was washed twice with brine (50 mL), dried with Na2S04, filtered and concentrated in vacuo (33.34 g). The residue was dissolved in 750 mL dichloromethane, and washed with a pH 9 KHC03/K2C03 solution (2 x1 OOmL). The organic layer was washed twice with brine (50 mL), dried with Na2S04, filtered and concentrated in vacuo (23.4 g). The crude material was dissolved in approximately 25 mL MeOH resulting in an orange solution and placed in a freezer overnight to form a slurry. The mixture was filtered, washed with MeOH and dried in vacuo to yield 21 .959 g of the title compound as a white solid. HRMS calculated for C27H34N405 495.2607, found (ESI, [M + H]+), 495.2607, retention time = 3.717 min. CHN analysis: calculated (results). C 65.57 (65.17), H 6.93 (6.64), N 1 1 .33 (1 1 .39). Alternate procedure 2To [4-(4-methoxy-benzoyl)-piperidin-1 -yl]-acetic acid (306 mg, 0.85 mmol) in DMF (3 ml.) was added with HATU (485 mg, 1.28 mmol) and DIEA (0.37 ml_, 275 mg, 2.12 mmol). This was sonicated, stirred for 30 min and then 2-[(cyclopropylmethyl-amino)- methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (200 mg, 0.85 mmol) in 1 ml_ DMF was added to the mixture. Then it was stirred at room temperature for 16 hours and the mixture was concentrated to dryness. This was purified by silica gel column (eluted with 0-10percent methanol in dichloromethane) followed by trituration with methanol to give a white solid as the title compound (93 mg, 0.19 mmol, 22percent yield), m/z = 495.3 (M+H).
Reference: [1] Patent: WO2013/12723, 2013, A1, . Location in patent: Page/Page column 99-101
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6495 - 6511
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