Phthalimide potassium salt → (2-Aminomethyl-quinazolin-4-yl)-(3-chloro-4-methoxy-phenyl)-methyl-amine

HRID 1876218Notes

Reaction equation

HRID 1876218 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH2:21][N:22]3C(=O)C4C(=CC=CC=4)C3=O)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[C:34]1C=C(N(C2C3C(=CC=CC=3)N=C(CCl)N=2)C)C=CC=1OC.C1(=O)NC(=O)C2=CC=CC=C12.[K]>CN(C=O)C>[NH2:22][CH2:21][C:13]1[N:12]=[C:11]([N:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[CH3:34])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 3

HCID 24194345Phthalimide potassium saltHCID 59242090(3-Chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-methyl-amineHCID 685163012-[4-(3-Chloro-4-methoxy-phenylamino)-quinazolin-2-ylmethyl]-isoindole-1,3-dione

Product 1

HCID 59242078(2-Aminomethyl-quinazolin-4-yl)-(3-chloro-4-methoxy-phenyl)-methyl-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-(3-Chloro-4-methoxy-phenylamino)-quinazolin-2-ylmethyl]-isoindole-1,3-dione: The title compound was prepared from (3-chloro-4-methoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-methyl-amine (428 mg, 1.1 mmol) and potassium phthalimide (453 mg, 2.4 mmol) in DMF (3.7 mL) by a procedure similar to Example 203d. 1H NMR (DMSO-d6) δ 7.98-7.90 (m, 4H), 7.62-7.60 (m, 2H), 7.48 (d, 1H), 7.2-7.13 (m, 3H), 6.96-6.93 (d, 1H), 4.96 (s, 2H), 3.87 (s, 3H), 3.28 (s, 3H); LC-MS (ESI+; 459 ([M+H]+)).

Sources & evidence

ORD record
ord-c29cd6868c7346438b016d50ad2f9e47
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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