Benzofuran-7-amine → 4-(benzofuran-7-ylamino)-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline dihydrochloride

HRID 1826296Notes

Reaction equation

HRID 1826296 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[C:31]2[O:30][CH:29]=[CH:28][C:27]=2[CH:26]=[CH:25][CH:24]=1>>[ClH:1].[ClH:1].[O:30]1[C:31]2[C:23]([NH:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:20][CH3:21])=[CH:9][C:10]=4[O:12][CH:13]4[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]4)[N:5]=[CH:4][N:3]=3)=[CH:24][CH:25]=[CH:26][C:27]=2[CH:28]=[CH:29]1

Participants

3

Reactant 2

HCID 11217277Benzofuran-7-amineHCID 113812714-Chloro-7-methoxy-5-[(1-methylpiperidin-4-yl)oxy]quinazoline

Product 1

HCID 221407344-(benzofuran-7-ylamino)-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline dihydrochloride

Procedure

Using an analogous procedure to that described in Example 5, 4-chloro-7-methoxy-5-(N-methylpiperidin-4-yloxy)quinazoline was reacted with 7-aminobenzofuran to give the title compound, a portion of which was treated with a saturated methanolic ammonia solution. The mixture was filtered and the filtrate was evaporated to give the free base; NMR Spectrum: (CDCl3) 2.15–2.35 (m, 6H), 2.32 (s, 3H), 2.92 (m, 2H), 3.9 (s, 3H), 4.6 (m, 1H), 6.5 (d, 1H), 6.8 (d, 1H), 6.85 (d, 1H), 7.25–7.4 (m, 2H), 7.68 (d, 1H), 8.58 (d, 1H), 8.6 (s, 1H), 10.25 (br s, 1H); Mass Spectrum: M+H+ 405.

Sources & evidence

ORD record
ord-d5cfea2fc0b045e092de5c235edb6e91
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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