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

HRID 33856Notes

Reaction equation

HRID 33856 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][N:10]=[CH:9][C:8]=2[C:12]2[CH:29]=[CH:28][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.[CH3:30][NH:31][NH2:32]>>[CH3:30][N:11]1[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:28][CH:29]=2)[CH:9]=[N:10]1.[CH3:30][N:31]1[CH:9]=[C:8]([C:12]2[CH:29]=[CH:28][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[N:32]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 116537402-[4-(5-Pyridin-4-yl-1H-pyrazol-4-yl)-phenoxymethyl]-quinoline

Product 2

HCID 116108472-[4-(1-Methyl-3-pyridin-4-yl-1H-pyrazol-4-yl)-phenoxymethyl]-quinolineHCID 116826152-[4-(1-Methyl-5-pyridin-4-yl-1H-pyrazol-4-yl)-phenoxymethyl]-quinoline

Procedure

Following the procedure for the preparation of 2-[4-(5-Pyridin-4-yl-1H-pyrazol-4-yl)-phenoxymethyl]-quinoline but substituting methyl hydrazine provided the title compound and 2-[4-(1-Methyl-3-pyridin-4-yl-1H-pyrazol4-yl)-phenoxymethyl]-quinoline. 1H NMR (400 MHz, CDCl3) δ 8.66 (bs, 2 H), 8.17 (d, J=8.7 Hz, 1H), 8.05 (d, J=7.9 Hz, 1 H), 7.81 (d, J=8.3 Hz, 1H), 7.70 (m, 1 H), 7.63 (m, 2 H), 7.53 (t, J=7.1 Hz, 1 H), 7.21 (m, 2 H), 7.03 (d, J=9.1 Hz, 2H), 6.89 (d, J=8.7 Hz, 2H), 5.32 (s, 2H), 3.80 (s, 3H); MS: (M+H m/z=393.2).

Sources & evidence

ORD record
ord-6f9f3307679a4adb854d7e0ffa9d1418
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

Loading…