Piconol → HCID 22457794, compound

HRID 1383863Notes

Reaction equation

HRID 1383863 reaction equation
C[C:2]1([C:6](O)=O)[CH2:5][CH2:4][CH2:3]1.Cl[C:10]1[N:11]=[N:12][C:13](Cl)=[CH:14][C:15]=1[CH3:16].ClC1N=NC(Cl)=CC=1.[C:26]([NH:34][NH2:35])(=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:36][N:37]1[C:41]([CH2:42][OH:43])=[N:40][CH:39]=[N:38]1.OCC1C=CC=CN=1>>[CH3:16][C:15]1[C:10]2[N:11]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:34][N:35]=2)[N:12]=[C:13]([O:43][CH2:42][C:41]2[N:37]([CH3:36])[N:38]=[CH:39][N:40]=2)[C:14]=1[C:2]1([CH3:6])[CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 6

HCID 11474PiconolHCID 11955BenzoylhydrazineHCID 673313,6-DichloropyridazineHCID 879233,6-Dichloro-4-methylpyridazineHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 127574881-Methylcyclobutane-1-carboxylic acid

Product 1

HCID 22457794HCID 22457794, compound

Procedure

The compound was prepared using the procedures described in Example 102, Steps a), b) and c) with 1-methylcyclobutane carboxylic acid (U.S. Pat. No. 4,220,795) and 3,6-dichloro-4-methylpyridazine being used instead of cyclopentane carboxylic acid and 3,6-dichloropyridazine respectively in Step a), and benzoic acid hydrazide being used instead of 2-thiophene carboxylic acid hydrazide in Step b), and (2-methyl-2 H-1,2,4-triazol-3-yl)methanol (prepared using the conditions described in EP-A-421210) being used instead of 2-hydroxymethylpyridine in Step c). Data for the title compound: 1H NMR (360 MHz, CDCl3) δ1.54 (3 H, s), 1.76-1.84 (1 H, m), 2.04-2.16 (3 H, m), 2.46-2.53 (2 H, m), 2.64 (3 H, s), 3.94 (3 H, s), 5.53 (2 H, s), 7.46-7.56 (3 H, m), 7.93 (1 H, s), 8.34 (2 H, d, J=8 Hz); MS (ES+) m/e 390 [MH]+. Anal. Found C, 64.83; H, 5.82; N, 25.04. C21H23N7O requires C, 64.76; H, 5.95; N, 25.18%.

Workup

  1. customThe compound was prepared
  2. customprepared

Sources & evidence

ORD record
ord-31fae0b31da9410b9dfc0c6600c5c372
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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