Hydrazine → 6-(4-ethoxy-2-fluoro-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine

HRID 2375411Notes

Reaction equation

HRID 2375411 reaction equation
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH:5]([C:9](=O)[CH3:10])[C:6](=O)[CH3:7])(=O)[CH3:2].[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([F:25])[CH:19]=1)[CH3:16].[NH2:26][NH2:27]>>[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:1]([CH3:2])=[C:4]3[C:5]([C:9]([CH3:10])=[N:26][N:27]=[C:12]3[CH3:13])=[C:6]2[CH3:7])=[C:20]([F:25])[CH:19]=1)[CH3:16]

Participants

4

Reactant 3

HCID 9321HydrazineHCID 787303,4-Diacetyl-2,5-hexanedioneHCID 37344624-ethoxy-2-fluoroaniline

Product 1

HCID 102675836-(4-ethoxy-2-fluoro-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine

Procedure

Utilizing the general procedure outlined in Example 48, 1,1,2,2-tetraacetylethane (200 mg, 1.0 mol), 4-ethoxy-2-fluoro-phenyl amine (155 mg, 1.0 mmol) and hydrazine (50 μL) reacted to give 6-(4-ethoxy-2-fluoro-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine as yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.13 (t, 1H), 6.88 (m, 2H), 4.16 (q, 2H), 2.82 (s, 6H), 2.46 (s, 6H), 1.53 (t, 3H); MS (ESI) 314 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-40b2dd800b3a40caa867dffbc8145b9d
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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