Hydrazine → HCID 10380640, compound

HRID 2375395Notes

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

Participants

Reactant 2

HCID 9321Hydrazine

HCID 69277491HCID 69277491, compound

Product 1

HCID 10380640HCID 10380640, compound

Procedure

As outlined 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 1-bromo-propane (100 μL), in the presence of K2CO3 powder (50 mg), to afford 1-[4-acetyl-2,5-dimethyl-1-(4-propoxy-phenyl)-1H-pyrrol-3-yl]-ethanone: MS (ESI) 328 (M+H)+. Utilizing the general procedure outlined in Example 48, 1-[4-acetyl-2,5-dimethyl-1-(4-propoxy-phenyl)-1H-pyrrol-3-yl]-ethanone and hydrazine reacted to give 1,4,5,7-Tetramethyl-6-(4-propoxy-phenyl)-6H-pyrrolo[3,4-d]pyridazine as light yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.04 (d, 1H), 6.95 (br s, 1H), 6.91 (d, 1H), 4.03 (t, 2H), 2.85 (s, 6H), 2.42 (s, 6H), 1.86 (q, 2H), 1.79 (s, 3H), 1.09 (t, 3H); MS (ESI) 328 (M+H)+.

Workup

customreacted

Sources & evidence

ORD record: ord-d832c1bd831c4ae7bde75b4e775c70c4
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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