Sulfamide → 4-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-piperidine-1-sulfonic acid amide

HRID 2046928ノート

反応式

HRID 2046928 の反応式
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[S:32](N)([NH2:35])(=[O:34])=[O:33]>O1CCOCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:27][CH2:28][N:29]([S:32]([NH2:35])(=[O:34])=[O:33])[CH2:30][CH2:31]4)[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

参加物

4

反応物 2

HCID 82267SulfamideHCID 461964113-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 673638464-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-piperidine-1-sulfonic acid amide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine (8.0 mg, 0.0174 mmol), sulfamide (3.35 mg, 0.0349 mmol) and dioxane (2 mL) was heated to 90° C. overnight in a sealed tube. The solution was concentrated in vacuo, redissolved in MeOH and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.89 (d, J=7.1 Hz, 3 H), 2.09-2.25 (m, 4 H), 2.76-2.91 (m, 2H), 3.78 (d, J=12.4 Hz, 2 H), 4.30 (dt, J=10.4, 5.3 Hz, 1 H), 5.29 (q, J=7.4 Hz, 1 H), 7.15-7.23 (m, 1 H), 7.36 (d, J=1.5 Hz, 1 H), 7.38-7.53 (m, 2 H), 7.58 (s, 1 H), 7.92 (s, 1 H), 8.32 (d, J=1.8 Hz, 1 H). MS (ES+): m/z 537.02 (100) [MH+]. HPLC: tR=3.36 min (ZQ3, polar—5 min).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

出典と根拠

ORDレコード
ord-452a7b96ce444a7e86095266981f81db
出典データセット
uspto-grants-2013_11
特許番号
US08592448B2

反応ノート

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