Hydrogen Bromide → HCID 86267405, 화합물

HRID 709981노트

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HRID 709981 반응식
[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]

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 90416592HCID 90416592, 화합물

생성물 1

HCID 86267405HCID 86267405, 화합물수율 42.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
90 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-34fb71747f064385aed39926d2bca98b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181223B2

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