Hydrazine → HCID 11722755, compound

HRID 2375396Notes

Reaction equation

[C:1]([C:4]1[C:5]([C:21](=O)[CH3:22])=[C:6]([CH3:20])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]=[CH2:19])=[CH:12][CH:11]=2)[C:8]=1[CH3:9])(=O)[CH3:2].[NH2:24][NH2:25]>>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[C:8]([CH3:9])=[C:4]3[C:5]([C:21]([CH3:22])=[N:24][N:25]=[C:1]3[CH3:2])=[C:6]2[CH3:20])=[CH:11][CH:12]=1)[CH:18]=[CH2:19]

Participants

Reactant 2

HCID 9321Hydrazine

HCID 69274023HCID 69274023, compound

Product 1

HCID 11722755HCID 11722755, compound

Procedure

As in Example 65, 1-[4-acetyl-1-(4-hydroxy-2-methyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (Example 52, 20 mg) reacted with allyl bromide (50 μL), in the presence of K2CO3 (50 mg), to afford 1-[4-acetyl-1-(4-allyloxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone: MS (ESI) 326 (M+H)+. Utilizing the general procedure outlined in Example 48, 1-[4-acetyl-1-(4-allyloxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (20 mg) and hydrazine (50 μL) reacted to give 6-(4-allyloxy-phenyl)-1,4,5,7-tetramethyl-6H-pyrrolo[3,4-d]pyridazine as light yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.04 (m, 1H), 6.98 (s, 1H), 6.94 (m, 1H), 6.13 (m, 1H), 5.52 (d, 1H), 5.39 (d, 1H), 4.64 (d, 2H), 2.81 (s, 6H), 2.35 (s, 6H), 1.84 (s, 3H); MS (ESI) 322 (M+H)+.

Workup

customreacted

Sources & evidence

ORD record: ord-b4ee685e393f496eb0fab7f3156dbfbc
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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