Hydrazine hydrate (1:1) → 4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1091747노트

반응식

HRID 1091747 반응식
O.[NH2:2][NH2:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([C:14]2[C:15]([C:20](OC)=[O:21])=[CH:16][NH:17][C:18]=2[CH3:19])=O)=[CH:7][C:6]=1[C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][CH3:33])[CH2:28][CH2:27]1)=[O:25]>C(O)(=O)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:14]3[C:15](=[CH:16][NH:17][C:18]=3[CH3:19])[C:20](=[O:21])[NH:2][N:3]=2)=[CH:7][C:6]=1[C:24]([N:26]1[CH2:27][CH2:28][CH:29]([O:32][CH3:33])[CH2:30][CH2:31]1)=[O:25]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 57791840Methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-5-methyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 1361018784-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one수율 19.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Hydrazine hydrate (0.023 mL, 0.31 mmol) was added to methyl 4-(2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetyl)-5-methyl-1H-pyrrole-3-carboxylate (62) (0.117 g, 0.28 mmol) in acetic acid (4 mL). The resulting solution was stirred at room temperature for 2 days. The resulting mixture was evaporated to dryness and the residue was azeotroped with toluene to afford crude product, which was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the desired compound (0.022 g, 19.65% yield); 1H NMR (400.132 MHz, DMSO) δ 1.21 (1H, m), 1.34 (1H, m), 1.62 (1H, m), 1.77 (1H, m), 2.25 (3H, s), 2.96 (1H, m), 3.15-3.36 (6H, m), 3.82 (1H, s), 4.05 (2H, s), 7.07-7.15 (2H, m), 7.19 (1H, m), 7.33 (1H, s), 11.22 (1H, s), 12.15 (1H, s); m/z (LC-MS, ESI+), RT=1.39 min (M+H=399.15).

후처리

  1. customThe resulting mixture was evaporated to dryness
  2. customthe residue was azeotroped with toluene
  3. customto afford crude product, which
  4. customwas purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  5. additionFractions containing the desired compound
  6. customwere evaporated to dryness

출처 및 근거

ORD 기록
ord-a2fdf5f311b544cab5884698dee3bce1
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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