Hydrogen Bromide → HCID 86267405、化合物

HRID 709981ノート

反応式

HRID 709981 の反応式
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([O:11]C)[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26]4[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=4)[CH:21]=3)=[C:15]([CH3:32])[N:14]=2)=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br>C(O)(=O)C>[CH:1]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26]4[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=4)[CH:21]=3)=[C:15]([CH3:32])[N:14]=2)=[CH:7][N:6]=1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 260Hydrogen BromideHCID 90416592HCID 90416592、化合物

生成物 1

HCID 86267405HCID 86267405、化合物収率 42.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

A solution of N-isopropyl-4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.063 g, 0.14 mmol) in acetic acid (5 mL) was treated with HBr (0.066 mL, 0.58 mmol), heated at 90° C. for 4 h, cooled to RT and quenched with ice water. The solution was treated with NaHCO3 and NaCl, extracted with 1:1 THF/EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN (1 mL), allowed to stand at RT and the resulting solid was collected via filtration to afford 2-(isopropylamino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (25 mg, 38%). 1H NMR (400 MHz, DMSO-d6): δ 10.8 (br s, 1H), 8.68 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.27 (s, 1H), 8.26 (s, 1H), 7.96 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.67 (br s, 1H), 6.61 (d, J=5.6 Hz, 1H), 4.07 (m, 1H), 3.85 (s, 3H), 2.34 (s, 3H), 1.17 (d, J=6.5 Hz, 6H); MS (ESI) m/z: 418.2 (M+H+).

後処理

  1. temperaturecooled to RT
  2. customquenched with ice water
  3. additionThe solution was treated with NaHCO3 and NaCl
  4. extractionextracted with 1:1 THF/EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionThe material was treated with MeCN (1 mL)
  8. customto stand at RT
  9. filtrationthe resulting solid was collected via filtration

出典と根拠

ORDレコード
ord-34fb71747f064385aed39926d2bca98b
出典データセット
uspto-grants-2015_11
特許番号
US09181223B2

反応ノート

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