Hydrazine hydrate (1:1) → 4-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorobenzyl)-5,6,7-trimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1091740ノート

反応式

HRID 1091740 の反応式
O.[NH2:2][NH2:3].[CH2:4]([O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([C:15]2[CH:16]=[C:17]([CH2:22][C:23]([C:25]3[C:26]([C:33]([O:35]C)=O)=[C:27]([CH3:32])[N:28]([CH3:31])[C:29]=3[CH3:30])=O)[CH:18]=[CH:19][C:20]=2[F:21])=[O:14])[CH2:9][CH2:8]1)[CH3:5]>C(O)(=O)C>[CH2:4]([O:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][C:20]=2[F:21])[CH2:22][C:23]2[C:25]3[C:26](=[C:27]([CH3:32])[N:28]([CH3:31])[C:29]=3[CH3:30])[C:33](=[O:35])[NH:2][N:3]=2)=[O:14])[CH2:11][CH2:12]1)[CH3:5]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 57791827Methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate

生成物 1

HCID 577917774-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorobenzyl)-5,6,7-trimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one収率 32.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Hydrazine hydrate (0.028 mL, 0.38 mmol) was added to methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylate (55) (0.158 g, 0.34 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 the 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 (0.049 g, 32.3% yield); 1H NMR (400.132 MHz, DMSO) δ 1.11 (3H, t), 1.29 (1H, m), 1.41 (1H, m), 1.72 (1H, m), 1.86 (1H, m), 2.29 (3H, s), 2.60 (3H, s), 3.05 (1H, m), 3.28 (3H, s), 3.46 (2H, m), 3.53 (3H, s), 3.96 (1H, m), 4.12 (2H, s), 7.16-7.28 (3H, m), 11.17 (1H, s); m/z (LC-MS, ESI+), RT=1.78 min (M+H=441.11).

後処理

  1. customThe resulting mixture was evaporated to dryness
  2. customthe residue was azeotroped with toluene
  3. customto afford the 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

出典と根拠

ORDレコード
ord-0e198fc6d4fa46c4a0e8f20a5508e665
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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