Hydrochloric Acid → 4-(2,3-Methylenedioxyanilino)-5-(4-methylpiperazin-1-yl)-7-(2-pyrrolidin-1-ylethoxy)quinazoline trihydrochloride

HRID 641782Notes

Reaction equation

HRID 641782 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:9][C:10]=2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[N:5]=[CH:4][N:3]=1.[CH2:27]1[O:36][C:35]2[C:29](=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH2:31])[O:28]1.[ClH:37]>C(O)(C)C>[ClH:1].[ClH:37].[ClH:1].[CH2:27]1[O:36][C:35]2[C:29](=[C:30]([CH:32]=[CH:33][CH:34]=2)[NH:31][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:9][C:10]=3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[N:5]=[CH:4][N:3]=2)[O:28]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 103131651,3-Benzodioxol-4-amineHCID 221408074-Chloro-5-(4-methylpiperazin-1-yl)-7-(2-pyrrolidin-1-ylethoxy)quinazoline

Product 1

HCID 221407774-(2,3-Methylenedioxyanilino)-5-(4-methylpiperazin-1-yl)-7-(2-pyrrolidin-1-ylethoxy)quinazoline trihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using an analogous procedure to that described in Example 5, 4-chloro-5-(4-methylpiperazin-1-yl)-7-(2-pyrrolidin-1-ylethoxy)quinazoline (0.11 g) was reacted with 2,3-methylenedioxyaniline (0.045 g) in the presence of a 6M solution of hydrogen chloride in isopropanol to give the title compound, as a trihydrochloride salt (0.105 g), a portion of which was converted into the free base using an analogous procedure to that described in Example 3. The free base gave the following characterising data: NMR Spectrum: (CDCl3) 1.78 (br s, 4H), 2.3 (s, 3H), 2.5 (m, 2H), 2.6 (br s, 4H), 2.8 (d, 2H), 2.95 (m, 4H), 3.08 (d, 2H), 4.18 (m, 2H), 5.98 (s, 2H), 6.6 (d, 1H), 6.86 (m, 1H), 6.94 (s, 1H), 8.06 (d, 1H), 8.5 (s, 1H), 11.8 (s, 1H); Mass Spectrum: M+H+ 477.

Sources & evidence

ORD record
ord-a9e1739c130143f895a2ce848e5969f9
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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