4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-nitrophthalazin-1(2H)-one → 5-amino-4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one

HRID 1091728ノート

反応式

HRID 1091728 の反応式
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[N+:17]([O-])=O)[C:10](=[O:20])[NH:9][N:8]=2)=[CH:4][C:3]=1[C:23]([N:25]1[CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]1)=[O:24]>[Pd].C(O)C>[NH2:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:7]([CH2:6][C:5]1[CH:21]=[CH:22][C:2]([F:1])=[C:3]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)=[O:24])[CH:4]=1)=[N:8][NH:9][C:10]2=[O:20]

参加物

4

反応物 1

HCID 577917724-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-nitrophthalazin-1(2H)-one

生成物 1

HCID 577918455-amino-4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one収率 29.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)-5-nitrophthalazin-1 (2H)-one (45) (40 mg, 0.09 mmol) was added to 5% palladium on carbon (4 mg, 0.04 mmol) in ethanol (7 ml) at 25° C. under air. The resulting mixture was hydrogenated at 25° C. for 22 hours. The catalyst was filtered and washed with ethanol and the solvent evaporated to a pale brown gum. The crude product 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 material as a beige solid (11 mg, 29.5% yield); 1H NMR (400.132 MHz, DMSO) δ 1.66-1.81 (2H, m), 1.86-1.96 (2H, m), 3.10-3.19 (1H, m), 3.36 (3H, s), 3.44-3.50 (2H, m), 3.55-3.64 (1H, m), 3.91-3.99 (1H, m), 4.08 (2H, s), 4.44 (2H, s), 6.99 (1H, d), 7.05-7.10 (1H, m), 7.23-7.28 (2H, m), 7.50-7.54 (1H, m), 7.94 (1H, d), 9.95 (1H, s); m/z (LC-MS, ESI+), RT=1.50 (M+H 411.3).

後処理

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe solvent evaporated to a pale brown gum
  4. customThe crude product was 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

出典と根拠

ORDレコード
ord-614adb28d4ef4d019341417b6c90a96f
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

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