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

HRID 2046925노트

반응식

HRID 2046925 반응식
[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[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[S:27](N)([NH2:30])(=[O:29])=[O:28]>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[CH2:22][CH2:23][N:24]([S:27]([NH2:30])(=[O:29])=[O:28])[CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

참가 물질

4

반응물 2

HCID 82267SulfamideHCID 673640813-[1-(2,6-Dichloro-3-fluorophenyl)-ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 674012854-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-sulfonic acid amide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (10.0 mg, 0.0256 mmol), sulfamide (4.92 mg, 0.0512 mmol) and dioxane (2 mL) was heated to 90° C. for 16 h 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=1.87 (d, J=7.1 Hz, 3 H), 2.40-2.60 (m, 2 H), 3.32-3.35 (m, 2 H), 3.77 (q, J=2.6 Hz, 2 H), 5.26 (q, J=7.1 Hz, 1 H), 5.90-5.96 (m, 1 H), 7.19 (t, J=8.6 Hz, 1 H), 7.29 (s, 1 H), 7.37 (d, J=1.5 Hz, 1 H), 7.42 (br. s., 1 H), 8.28 (br. s., 1 H). MS (ES+): m/z 469.00 (100) [MH+]. HPLC: tR=3.42 min (ZQ3, polar—5 min).

후처리

  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

출처 및 근거

ORD 기록
ord-68426c81c1d544b79b9b7e1209532f6a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592448B2

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