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

HRID 33871Notes

Reaction equation

[N:1]1[C:10]2C(=CC=CC=2)C=C[CH:2]=1.C[NH:12]N.[Cl:14][C:15]1[CH:20]=[C:19]([CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:26][CH:25]=2)=O)[CH:18]=[CH:17][N:16]=1>>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]2[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)=[CH:26][CH:25]=3)=[N:12][N:1]([CH3:10])[CH:2]=2)[CH:18]=[CH:17][N:16]=1

Participants

Reactant 3

HCID 6061Methylhydrazine

HCID 7047Quinoline

HCID 862493242-(2-Chloro-pyridin-4-yl)-1-[4-(quinolin-2-ylmethoxy)-phenyl]-ethanone

Product 1

HCID 115536722-[4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-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 2-(2-Chloro-pyridin-4-yl)-1-[4-(quinolin-2-ylmethoxy)-phenyl]-ethanone provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.19 (m, 2 H), 8.07 (d, J=8.3 Hz, 1 H), 7.83 (d, J=8.3 Hz, 1 H), 7.74 (t, J=8.3 Hz, 1H), 7.67 (d, J=8.3 Hz, 1 H), 7.58 (s, 1H), 7.55 (t, J=8.3 Hz, 1 H), 7.36 (d, J=8.7 Hz, 2H), 7.20 (s, 1H), 7.03 (m, 3H), 5.40 (s, 2H) 3.95 (s, 3H); MS: (M+H m/z=427.0).

Sources & evidence

ORD record: ord-c5a143c0b7934784b8e795252febeb3a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Reaction notes

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