Methylhydrazine → 2-[2-Chloro-4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

HRID 33882Notes

Reaction equation

HRID 33882 reaction equation
N1C=CC(C2[CH:11]=[N:10][NH:9]C=2C2C=CC(CCC3C=CC4C(=CC=CC=4)N=3)=CC=2)=CC=1.[CH3:30]NN.[Cl:33][C:34]1[CH:35]=[C:36]([C:52](=O)[CH2:53][C:54]2[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=2)[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]=1>>[Cl:33][C:34]1[CH:35]=[C:36]([C:52]2[C:53]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)=[CH:30][N:10]([CH3:11])[N:9]=2)[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][C:42]1[CH:51]=[CH:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[N:43]=1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 115670052-{2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenyl]-ethyl}-quinolineHCID 685763001-[3-Chloro-4-(quinolin-2-ylmethoxy)-phenyl]-2-pyridin-4-yl-ethanone

Product 1

HCID 115826962-[2-Chloro-4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

Procedure

Following the procedure for the preparation of 2-{2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenyl]-ethyl}-quinoline but substituting methyl hydrazine and 1-[3-Chloro-4-(quinolin-2-ylmethoxy)-phenyl]-2-pyridin-4-yl-ethanone provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6.2 Hz, 2 H), 8.21 (d, J=8.3 Hz, 1 H), 8.04 (d, J=7.5 Hz, 1H), 7.83 (d, J=8.3 Hz, 1 H), 7.78 (d, J=8.7 Hz, 1 H), 7.72 (m, 1H), 7.56 (m, 3 H), 7.21 (m, 1H), 7.14 (d, J=6.2 Hz, 2 H), 6.97 (d, J=8.7 Hz, 1 H), 5.46 (s, 2H), 3.95 (s, 3H); MS: (M+H m/z=427.1).

Sources & evidence

ORD record
ord-5944b15bd1c24209b6a9aa4ba91eb1e3
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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