2-Methylpyrrolidine → 1-(Benzo[d][1,3]dioxol-5-yl)-n-(6-(4-(2-methylpyrrolidin-1-ylsulfonyl)phenyl)pyridin-2-yl)cyclopropanecarboxamide

HRID 17958

반응식

HRID 17958 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=5)[CH:19]=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:32][CH:33]1[CH2:37][CH2:36][CH2:35][NH:34]1>CCN(C(C)C)C(C)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([S:28]([N:34]6[CH2:35][CH2:36][CH2:37][CH:33]6[CH3:32])(=[O:30])=[O:29])=[CH:24][CH:23]=5)[N:21]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

4

반응물 2

HCID 130032-MethylpyrrolidineHCID 591661084-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzene-1-sulfonyl chloride

생성물 1

HCID 591661421-(Benzo[d][1,3]dioxol-5-yl)-n-(6-(4-(2-methylpyrrolidin-1-ylsulfonyl)phenyl)pyridin-2-yl)cyclopropanecarboxamide

시약·촉매·용매 1

HCID 81531Diisopropylethylamine용매

실험 절차

4-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzene-1-sulfonyl chloride (˜35 μmol, 400 μl solution in chloroform) was treated with 2-methylpyrrolidine followed by the addition of DIEA (100 μl). The reaction mixture was kept at room temperature for 1 h, concentrated, then diluted with DMSO (400 μl). The resulting solution was subjected to HPLC purification. Fractions containing the desired material were combined and concentrated in vacuum centrifuge at 40° C. to provide the trifluoroacetic salt of target material (ESI-MS m/z calc. 505.0. found 505.9 (M+1), retention time 4.06 min). 1H NMR (250 MHz, DMSO-d6) δ 1.15 (m. 2H), δ 1.22 (d, 3H, J=6.3 Hz), δ 1.41-1.47 (m, 2H), δ 1.51 (m, 2H), δ 1.52-1.59 (m, 2H), δ 3.12 (m, 1H), δ 3.33 (m, 1H), δ 3.64 (m, 1H), δ 6.07 (s, 2H), δ 6.96-7.06 (m, 2H), δ 7.13 (d, 1H, J=1.3 Hz), δ 7.78 (d, 1H, J=8.2 Hz), δ 7.88 (d, 2H, J=8.5 Hz), δ 7.94 (t, 1H, J=8.2 Hz), δ 8.08 (d, 1H, J=8.2 Hz), δ 8.16 (d, 2H, J=8.5 Hz), δ 8.53 (s, 1H).

후처리

  1. concentrationconcentrated
  2. additiondiluted with DMSO (400 μl)
  3. customThe resulting solution was subjected to HPLC purification
  4. additionFractions containing the desired material
  5. concentrationconcentrated in vacuum centrifuge at 40° C.
  6. customto provide the trifluoroacetic salt of target material (ESI-MS m/z calc. 505.0. found 505.9 (M+1), retention time 4.06 min)

출처 및 근거

ORD 기록
ord-11af5d9e3628491db579b27aa3da13be
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741321B2

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