Chloroacetyl chloride → 6-[1-(Chloroacetyl)piperidin-3-yloxy]4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline

HRID 1948959Notes

Reaction equation

HRID 1948959 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.Cl.[Cl:8][C:9]1[C:10]([F:35])=[C:11]([CH:32]=[CH:33][CH:34]=1)[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:30][CH3:31])=[C:20]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[CH:21]=2)[N:16]=[CH:15][N:14]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:26]1[CH2:27][CH2:28][CH2:29][CH:24]([O:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][C:19]=2[O:30][CH3:31])[N:16]=[CH:15][N:14]=[C:13]3[NH:12][C:11]2[CH:32]=[CH:33][CH:34]=[C:9]([Cl:8])[C:10]=2[F:35])[CH2:25]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 685224574-(3-Chloro-2-fluoroanilino)-7-methoxy-6-(piperidin-3-yloxy)quinazoline dihydrochloride

Product 1

HCID 685236386-[1-(Chloroacetyl)piperidin-3-yloxy]4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Chloroacetyl chloride (89 μl) was added to a solution of 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-(piperidin-3-yloxy)quinazoline dihydrochloride (469 mg; prepared as described in Example 45) and diisopropylethylamine (700 μl) in methylene chloride (15 ml) that was cooled to 0° C. The mixture was stirred at room temperature for 2 hours to give 6-[1-(chloroacetyl)piperidin-3-yloxy]-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline; Mass Spectrum: (M+H)+ 479.

Sources & evidence

ORD record
ord-112612c967624e0a8e0133118d539d7c
Source dataset
uspto-grants-2013_03
Patent number
US08399667B2

Reaction notes

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