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

HRID 1091738Notes

Reaction equation

HRID 1091738 reaction equation
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:32]([O:34]C)=O)=[C:27]([CH3:31])[NH:28][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[CH2:12][CH2:11][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]([CH3:31])[NH:28][C:29]=3[CH3:30])[C:32](=[O:34])[NH:2][N:3]=2)=[O:14])[CH2:9][CH2:8]1)[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57791805methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 1361018824-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorobenzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-oneYield 58.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrazine hydrate (0.037 mL, 0.49 mmol) was added to methyl 4-(2-(3-(4-ethoxypiperidine-1-carbonyl)-4-fluorophenyl)acetyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (53) (0.200 g, 0.45 mmol) in acetic acid (8 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 a crude gum, which was triturated with a mixture of NMP, DMSO and water to give a solid which was collected by filtration, washed with ether and dried under vacuum to give the desired compound as a white solid (0.112 g, 58.4% yield); 1H NMR (400.132 MHz, DMSO) δ 1.11 (3H, t), 1.29 (1H, m), 1.42 (1H, m), 1.71 (1H, m), 1.86 (1H, m), 2.27 (3H, s), 2.51 (3H, s), 3.04 (1H, m), 3.24-3.39 (2H, m), 3.46 (2H, m), 3.52 (1H, m), 3.97 (1H, s), 4.07 (2H, s), 7.13-7.30 (3H, m), 11.07 (1H, s), 11.94 (1H, s); m/z (LC-MS, ESI+), RT=1.62 min (M+H=427.12).

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. customthe residue was azeotroped with toluene
  3. customto afford a crude gum, which
  4. customwas triturated with a mixture of NMP, DMSO and water
  5. customto give a solid which
  6. filtrationwas collected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-848e261d214d444a9ce811fcfbf68e1a
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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