4-Fluorophenylhydrazine hydrochloride → HCID 178434457, compound

HRID 2241217Notes

Reaction equation

HRID 2241217 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([CH3:26])=[N:9]2)=CC=1.[CH3:29][N:30]1[C:35](=[O:36])[C:34]([C:37](O)=[O:38])=[CH:33][CH:32]=[N:31]1.Cl.FC1C=CC(NN)=CC=1>>[F:25][C:19]1[CH:20]=[C:21]([NH:24][C:37]([C:34]2[C:35](=[O:36])[N:30]([CH3:29])[N:31]=[CH:32][CH:33]=2)=[O:38])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:8][N:9]=[C:10]([CH3:26])[C:11]=12

Participants

4

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 224986362-Methyl-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 685133074-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

Product 1

HCID 178434457HCID 178434457, compound

Procedure

Prepared by 2-step process from 3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (prepared as in Example 5, Step D) and 2-methyl-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (prepared according to the 3-step procedure of Example 19, Steps A-C, substituting methylhydrazine for 1-(4-fluorophenyl)hydrazine hydrochloride) according to the procedure of Example 21, Steps A and B. The crude material was purified by silica gel flash column chromatography (3% MeOH in CH2Cl2) to afford 17 mg (64% for 2-step process) of the desired product. LRMS (ESI pos) m/e 395.2 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.30 (d, 1H), 8.25 (d, 1H), 8.17 (d, 1H), 8.02 (dd, 1H), 7.51 (m, 1H), 7.37 (t, 1H), 6.27 (d, 1H), 3.79 (s, 3H), 2.75 (s, 3H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −128.3.

Workup

  1. customprepared
  2. customThe crude material was purified by silica gel flash column chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-40981f6083d74cb1bddfdad296e0585e
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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