Hydrazine → HCID 57826781, 화합물

HRID 1961278노트

반응식

HRID 1961278 반응식
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:38])[C:6]=1[C:7]1[CH:8]=[C:9]([C:13]([NH:15][C@H:16]([CH2:26][N:27]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)=[O:14])[O:10][C:11]=1[CH3:12].NN>CO>[NH2:27][CH2:26][C@@H:16]([NH:15][C:13]([C:9]1[O:10][C:11]([CH3:12])=[C:7]([C:6]2[N:5]([CH3:38])[N:4]=[CH:3][C:2]=2[Cl:1])[CH:8]=1)=[O:14])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=1

참가 물질

4

반응물 2

HCID 9321HydrazineHCID 57826727HCID 57826727, 화합물

생성물 1

HCID 57826781HCID 57826781, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-{(1S)-2-(3,4-difluorophenyl)-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}-5-methyl-2-furancarboxamide (210 mg, 0.39 mmol) in methanol (5 ml) at 25° C. was added hydrazine (0.02 ml, 0.78 mmol) dropwise. After 12 h, the solution was concentrated, dry loaded onto silica and purified by column chromatography (5% MeOH in DCM (1% NH4OH)). The free base was converted to the HCl salt by addition of excess 4M HCl in dioxane (1 ml) to the residue in MeOH (2 ml) affording the HCl salt of the title compound as an off-white solid: LC-MS (ES) m/z 409(M+H)+, 1H NMR (400 MHz, MeOD) δ ppm 2.38 (s, 3H) 2.98 (d, J=9.35 Hz, 1H) 3.01 (d, J=5.56 Hz, 1H) 3.23 (dd, J=13.01, 8.97 Hz, 2H) 3.73-3.83 (m, 3H) 4.56 (d, J=9.35 Hz, 1H) 7.17 (s, 1H) 7.18-7.32 (m, 3H) 7.57 (s, 1H).

후처리

  1. concentrationthe solution was concentrated
  2. customdry loaded onto silica
  3. custompurified by column chromatography (5% MeOH in DCM (1% NH4OH))
  4. additionThe free base was converted to the HCl salt by addition of excess 4M HCl in dioxane (1 ml) to the residue in MeOH (2 ml)

출처 및 근거

ORD 기록
ord-fcdc70cfb48244cc92acf50c1f0b8476
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410158B2

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