Acetone → 3-(((4-(3-Chloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yl)methyl)(methyl)amino)-1-isopropylazetidine-3-carboxamide

HRID 1867744Notes

Reaction equation

HRID 1867744 reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:32])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH3:31])=[C:17]([CH2:20][N:21]([CH3:29])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][NH:24][CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:33][C:34]([CH3:36])=O>>[Cl:2][C:3]1[C:4]([F:32])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH3:31])=[C:17]([CH2:20][N:21]([CH3:29])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][N:24]([CH:34]([CH3:36])[CH3:33])[CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 690474023-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]azetidine-3-carboxamide hydrochloride salt

Product 1

HCID 115621713-(((4-(3-Chloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yl)methyl)(methyl)amino)-1-isopropylazetidine-3-carboxamideYield 50%

Procedure

3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]azetidine-3-carboxamide hydrochloride salt Example 74 was coupled with acetone using the same method as for the equivalent step in Example 76 to give the title product (50 mg, 50%) as a white powder; 1H NMR Spectrum: (CDCl3) 0.95 (d, 6H), 2.42 (s, 3H), 2.49 (brs, 1H), 3.24 (brs, 2H), 3.63 (d, 2H), 3.97 (m, 5H), 5.32 (brs, 1H), 7.14 (m, 2H), 7.24 (s, 1H), 7.65 (brs, 1H), 7.75 (brs, 1H), 7.99 (s, 1H), 8.54 (brs, 1H), 8.73 (s, 1H); Mass Spectrum: (M+H)+ 487.

Sources & evidence

ORD record
ord-6f7590755cb14686b22e0c936adab622
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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