Morpholine → N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 405841ノート

反応式

HRID 405841 の反応式
CS(O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([NH:19][C:20]([C:22]3[N:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]4=[N:24][CH:23]=3)=[O:21])[CH:13]=2)[N:8]=1)(=O)=O.CCN(C(C)C)C(C)C.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C=O)C>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[C:7]([CH2:6][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[O:11][N:10]=2)=[CH:13][C:14]=1[NH:19][C:20]([C:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]2=[N:24][CH:23]=1)=[O:21]

参加物

5

反応物 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86677447(3-(3-(Imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate

生成物 1

HCID 71281207N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate (44) (21.4 mg, 0.05 mmol), DIEA (13.0 mg, 0.1 mmol) and morpholine (13.0 mg, 0.15 mmol) in DMF (1 mL) was heated at 80° C. for 4 hours. The crude product was purified by preparative HPLC to yield N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F22). 1H NMR (400 MHz, CD2Cl2) δ 9.60 (d, J=6.8 Hz, 1H), 8.60 (d, J=1.6 Hz, 1H), 8.45 (s, 1H), 8.06 (s, 1H), 7.89 (dd, J=2.0, 8.0 Hz, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.54 (m, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.15 (m, 1H), 3.93 (s, 2H), 3.75 (m, 4H), 2.67 (m, 4H), 2.48 (s, 3H). MS m/z 419.2 (M+1)+. Note: if HCl salt of morpholine (0.15 mmol) was used, AgNO3 (0.15 mmol) was needed to avoid replacement of OMs group by Cl.

後処理

  1. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-7720ea6c67a2464cbb53afd03a9b2432
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

反応ノート

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