3-Chloro-1-benzofuran-7-amine → 4-(3-Chlorobenzofuran-7-ylamino)-7-[3-(4-methylpiperazin-1-yl)propoxy]-5-tetrahydropyran-4-yloxyquinazoline dihydrochloride

HRID 1373309Notes

Reaction equation

HRID 1373309 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[CH:9][C:10]=2[O:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:5]=[CH:4][N:3]=1.[NH2:30][C:31]1[C:39]2[O:38][CH:37]=[C:36]([Cl:40])[C:35]=2[CH:34]=[CH:33][CH:32]=1>>[ClH:1].[ClH:40].[Cl:40][C:36]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([NH:30][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:19][CH2:20][CH2:21][CH2:22][N:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[CH:9][C:10]=4[O:12][CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[N:5]=[CH:4][N:3]=3)[C:39]=2[O:38][CH:37]=1

Participants

3

Reactant 2

HCID 221407493-Chloro-1-benzofuran-7-amineHCID 221408264-Chloro-7-[3-(4-methylpiperazin-1-yl)propoxy]-5-tetrahydropyran-4-yloxyquinazoline

Product 1

HCID 221407734-(3-Chlorobenzofuran-7-ylamino)-7-[3-(4-methylpiperazin-1-yl)propoxy]-5-tetrahydropyran-4-yloxyquinazoline dihydrochloride

Procedure

Using an analogous procedure to that described in Example 5, 4-chloro-7-[3-(4-methylpiperazin-1-yl)propoxy]-5-tetrahydropyran-4-yloxyquinazoline was reacted with 7-amino-3-chlorobenzofuran 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) 2.07 (m, 2H), 2.1 (m, 2H), 2.25 (m, 2H), 2.27 (s, 3H), 2.35–2.68 (m, 10H), 3.6 (t, 2H), 4.0–4.2 (m, 4H), 4.75 (m, 1H), 6.52 (s, 1H), 6.85 (s, 1H), 7.35 (m, 2H), 7.65 (s, 1H), 8.6 (s, 1H), 8.7 (d, 1H), 10.3 (s, 1H); Mass Spectrum: M+H+ 522 and 524.

Sources & evidence

ORD record
ord-6f4d0b6ad0e844e489c4921e97da174d
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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