Trifluoroacetic acid → 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

HRID 1431627ノート

反応式

HRID 1431627 の反応式
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:33]=1)=[C:5]([CH3:26])[C:6]([N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[N:7]2.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:33]=1)=[C:5]([CH3:26])[C:6]([N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)=[N:7]2

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 516892Sodium BicarbonateHCID 57449790Tert-butyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

The tert-butyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)-quinolin-2-yl)piperazine-1-carboxylate (32 mg, 0.059 mmol) was dissolved in DCM (1.0 mL) and cooled to 0° C. The trifluoroacetic acid (1.00 mL, 13.0 mmol) was then added and the reaction mixture was allowed to slowly warm to rt over a period of 1 h. The reaction was then cond to dryness. The crude TFA salt was treated with satd sodium bicarbonate solution. The organic layer was dried over sodium sulfate and the filtrate was cond to give 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 7.85 (1H, d, J=2.5 Hz), 7.63 (1H, d, J=2.2 Hz), 7.23 (1H, ddd, J=10.2, 2.5, 1.4 Hz), 6.79 (1H, d, J=12.9 Hz), 6.71 (1H, ddd, J=13.9, 8.8, 2.5 Hz), 6.49 (1H, t, J=2.3 Hz), 3.70-3.83 (4H, m), 3.19-3.32 (4H, m), 3.03-3.12 (4H, m), 2.92-3.03 (4H, m), 2.00 (3H, s). Mass Spectrum (ESI) m/e=441.2 (M+1).

後処理

  1. temperatureto slowly warm to rt over a period of 1 h
  2. dry with materialThe organic layer was dried over sodium sulfate

出典と根拠

ORDレコード
ord-a8b866f9868e49b9a6fa252a67bfd473
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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