HCID 178523501, 화합물 → HCID 178507516, 화합물

HRID 1093609노트

반응식

HRID 1093609 반응식
[N+:1]([C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:29])[CH2:14][NH:15][C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][N:19]=2)=[O:17])[CH2:9][CH2:8]1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13](=[O:29])[CH2:14][NH:15][C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:20][N:19]=2)=[O:17])[CH2:11][CH2:12]1

참가 물질

5

반응물 1

HCID 178523501HCID 178523501, 화합물

생성물 1

HCID 178507516HCID 178507516, 화합물수율 39%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-nitro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.07 g, 0.00016 mole) in a mixture of methanol (5 mL) and THF (5 mL) was added 10% Pd/C (0.01 g). The resulting mixture was stirred under an atmosphere of hydrogen for 30 minutes. The mixture was then filtered through celite, and the celite was washed with methanol. The combined organic layers were concentrated under reduced pressure. The resulting residue was re-crystallized from a hexane/chloroform mixture to afford 0.025 g (39%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-amino-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 420.2 (M+1)+, 96.9%, 1H NMR (DMSO-d6): δ 8.1 (bs, 1H), 7.8 (d, 2H), 7.5-7.3 (m, 3H), 7.1 (m, 1H), 6.85 (d, 1H), 6.7 (m, 2H), 6.5 (m, 1H), 4.7 (s, 2H), 4.6 (s, 1H), 4.2 (s, 2H), 3.9 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H), 1.4 (m, 2H).

후처리

  1. filtrationThe mixture was then filtered through celite
  2. washthe celite was washed with methanol
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. customThe resulting residue was re-crystallized from a hexane/chloroform mixture

출처 및 근거

ORD 기록
ord-f3385135ca8a4f6d82eec0ae69c7e23f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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