3-Bromoaniline → HCID 68903036, compound

HRID 2099382Notes

Reaction equation

HRID 2099382 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.[Br:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32].Cl.ClC1C=C(NC2C3C(=CC(OC4CCNCC4)=C(OC)C=3)N=CN=2)C=CC=1F>>[ClH:1].[Br:28][C:29]1[CH:30]=[C:31]([NH:32][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:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 115623-BromoanilineHCID 596829067-{[1-(Tert-butoxycarbonyl)-piperidin-4-yl]oxy}-4-chloro-6-methoxyquinazolineHCID 68904833HCID 68904833, compound

Product 1

HCID 68903036HCID 68903036, compound

Procedure

tert-Butyl 4-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]piperidine-1-carboxylate was coupled with 3-bromoaniline using an analogous process to that described in Example 21 (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-(3-bromophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine hydrochloride; 1H NMR Spectrum: (DMSO d6): 1.8-2.1 (m, 2H), 2.1-2.3 (m, 2H), 3.0-3.35 (m, 4H), 4.05 (s, 3H), 4.88 (m, 1H), 7.38-7.52 (m, 2H), 7.6 (s, 1H), 7.8 (d, 1H), 8.05 (s, 1H), 8.5 (s, 1H), 8.87 (s, 1H), 9.2 (bs, 2H), 11.7 (s, 1H); Mass Spectrum: (M+H)+ 431.

Sources & evidence

ORD record
ord-ba11d4bf96a84ebca2c32bbb05053108
Source dataset
uspto-grants-2009_08
Patent number
US07569577B2

Reaction notes

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