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

HRID 2375402Notes

Reaction equation

[C:1]([C:4]1[C:5]([C:23](=O)[CH3:24])=[C:6]([CH3:22])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][C:11]=2[O:19][CH2:20][CH3:21])[C:8]=1[CH3:9])(=O)[CH3:2].[NH2:26][NH2:27]>>[CH2:20]([O:19][C:11]1[CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:10]=1[N:7]1[C:8]([CH3:9])=[C:4]2[C:5]([C:23]([CH3:24])=[N:26][N:27]=[C:1]2[CH3:2])=[C:6]1[CH3:22])[CH3:21]

Participants

Reactant 2

HCID 9321Hydrazine

HCID 69277528HCID 69277528, compound

Product 1

HCID 498236616-(2,4-Diethoxyphenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine

Procedure

Utilizing the general procedure outlined in Example 65, 1-[4-acetyl-1-(2,4dihydroxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone prepared as in Example 70 (12 mg, 0.4 mmol) reacted with bromoethane (30 μL, excess), in the presence of K2CO3 (10 mg), to afford 1-[4-acetyl-1-(2,4-diethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone: MS (ESI) 344 (M+H)+. Utilizing the general procedure outlined in Example 48, 1-[4-acetyl-1-(2,4-diethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (4 mg) and hydrazine (5 μL) reacted to give 6-(2,4-diethoxy-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine as off-white solid: 1H NMR (CDCl3, 500 MHz) δ 7.03 (d, 1H), 6.67 (s, 1H), 6.64 (d, 1H), 4.15 (q, 1H), 4.04 (q, 1H), 2.89 (br s, 6H), 2.43 (s, 6H), 1.49 (t, 3H, 1.26 (t, 3H); MS (ESI) 340 (M+H)+.

Workup

customreacted

Sources & evidence

ORD record: ord-d2dbec1485814d909c2b7a8e76243df9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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