4-(Pyridin-3-Yloxy)Aniline → HCID 10345680, compound

HRID 1837379Notes

Reaction equation

HRID 1837379 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:23]#[N:24].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH:26]=1>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:5]=[CH:4][C:3]([C:23]#[N:24])=[C:2]2[NH:38][C:35]1[CH:34]=[CH:33][C:32]([O:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 31596314-(Pyridin-3-Yloxy)AnilineHCID 23498109HCID 23498109, compound

Product 1

HCID 10345680HCID 10345680, compoundYield 70.6%

Procedure

Following the procedure used to prepare Reference Example 22, a mixture of 4-chloro-6- methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile (200 mg, 0.58 mmol) and 4-(pyridin-3-yloxy)phenylamine (161.5 mg, 0.87 mmol) (Cacciola, J.; Fevig, J. M.; Stouten, P. F. W.; Alexander, R. S.; Knabb, R. M.; Wexler, R. W. Bioorg. Med. Chem. Let. 2000, 10, 1253) provides 203 mg of 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-{[4-(pyridin-3-yloxy)phenyl]amino}quinoline-3-carbonitrile, mp 182-184° C.

Workup

  1. customto prepare Reference Example 22

Sources & evidence

ORD record
ord-a2e3edcc33ac48ee83de9cf72113f059
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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