methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399789ノート

反応式

HRID 1399789 の反応式
[CH3:1][C:2]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[CH3:32])[C:5]2=[N:6][C:7]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:8][C:9]([C:10]([O:12]C)=[O:11])=[C:4]2[N:3]=1>[Li+].[OH-].C1COCC1>[CH3:1][C:2]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[C:23]=2[CH3:32])[C:5]2=[N:6][C:7]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[N:3]=1

参加物

4

反応物 1

HCID 89648239methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

生成物 1

HCID 716125532-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid収率 61.4%

試薬・触媒・溶媒 2

HCID 3939Lithium Hydroxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (310 mg, 0.69 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 50° C. for 8 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was purified by chromatography on silica gel eluted with MeOH/DCM=1/5 to afford the desired product as a gray solid (184 mg, 61%); LC/MS: MS (ES+) m/e 435 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.54 (s, 3H), 2.79 (s, 3H), 3.51 (s, 4H), 3.67 (s, 4H), 5.67 (s, 2H), 7.20 (d, J=10.2 Hz, 1H), 7.35 (t, J=7.8 Hz, 1H), 7.42 (s, 1H), 7.69 (d, J=10.2 Hz, 1H).

後処理

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (50 mL)
  4. filtrationIt was filtered
  5. customthe solid was purified by chromatography on silica gel
  6. washeluted with MeOH/DCM=1/5

出典と根拠

ORDレコード
ord-d9da61bff2cf49fa9fffe0174e3fdc98
出典データセット
uspto-grants-2014_12
特許番号
US08906910B2

反応ノート

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