5-Chloro-2-fluoroaniline → HCID 68906694, compound

HRID 2099383Notes

Reaction equation

HRID 2099383 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:28][C:29]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:30]=1[NH2:31].Cl.ClC1C=C(NC2C3C(=CC(OC4CCNCC4)=C(OC)C=3)N=CN=2)C=CC=1F>>[ClH:1].[Cl:36][C:33]1[CH:34]=[CH:35][C:29]([F:28])=[C:30]([NH:31][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH:15]4[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:32]=1

Participants

4

Reactant 3

HCID 750155-Chloro-2-fluoroanilineHCID 596829067-{[1-(Tert-butoxycarbonyl)-piperidin-4-yl]oxy}-4-chloro-6-methoxyquinazolineHCID 68904833HCID 68904833, compound

Product 1

HCID 68906694HCID 68906694, compound

Procedure

tert-butyl 4-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]piperidine-1-carboxylate was coupled with 2-fluoro-5-chloroaniline using an analogous process to that described in Example 22 (preparation of starting materials) for the preparation of N-(3-chloro-4-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine hydrochloride, to give N-(5-chloro-2-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine hydrochloride; 1H NMR Spectrum: (DMSO d6) 1.8-2.1 (m, 2H), 2.1-2.35 (m, 2H), 3.0-3.35 (m, 4H), 4.05 (s, 3H), 4.8-5.0 (m, 1H), 7.4-7.55 (m, 2H), 7.55-7.75 (m, 2H), 8.45 (s, 1H), 8.82 (s, 1H), 9.22 (bs, 2H), 11.94 (s, 1H); Mass Spectrum: (M+H)+ 403.

Sources & evidence

ORD record
ord-ee51e113a26848aeb20329da336ae932
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

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