N-methyl-2-pyrrolidone → HCID 86695066, compound

HRID 574342Notes

Reaction equation

HRID 574342 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20].CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.CN1C(=O)[CH2:36][CH2:35][CH2:34]1>>[CH3:34][C:35]1([CH3:36])[CH2:28][CH2:26][N:25]([C:2]2[N:7]3[N:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:10]=[C:6]3[N:5]=[C:4]([CH3:17])[C:3]=2[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:29][CH2:31]1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 86695067HCID 86695067, compound

Product 1

HCID 86695066HCID 86695066, compoundYield 85%

Procedure

To a solution of methyl 2-(7-chloro-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (100 mg, 0.316 mmol) and 4,4-dimethylpiperidine, HCl (47.3 mg, 0.316 mmol) in NMP (Volume: 3 mL) was added DIEA (0.220 mL, 1.263 mmol). The resulting mixture was stirred at r.t for 3 hrs. then purified by Pre-HPLC to afford methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (108 mg, 0.269 mmol, 85% yield). 1H-NMR (500 MHz, CDCl3) δ 1.14 (6 H, s), 1.68 (2 H, t), 2.63 (3 H, s), 3.62 (2 H, t), 3.82 (3 H, s), 7.55-7.57 (3 H, m), 8.24-8.26 (2 H, m).

Workup

  1. customthen purified by Pre-HPLC

Sources & evidence

ORD record
ord-4d83a0981fe447bd831240df335d8447
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

Loading…