Isopropylamine → N-(3-chloro-2-fluorophenyl)-6-[(isopropylamino)methyl]-7-methoxyquinazolin-4-amine

HRID 1867714Notes

Reaction equation

HRID 1867714 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][N:20](C(C)C)[C@H:21]([C:23](O)=O)[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C(F)=C(C=CC=1)NC1C2C(=CC(OC)=C(C=O)C=2)N=CN=1.C(N)(C)C>>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][NH:20][CH:21]([CH3:23])[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6363IsopropylamineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehydeHCID 57979815N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-isopropyl-L-alanine

Product 1

HCID 69047474N-(3-chloro-2-fluorophenyl)-6-[(isopropylamino)methyl]-7-methoxyquinazolin-4-amine

Procedure

The N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-isopropyl-L-alanine used as starting material was prepared as follows: 4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with isopropylamine using an analogous method to that described for the equivalent step in Example 1 to give N-(3-chloro-2-fluorophenyl)-6-[(isopropylamino)methyl]-7-methoxyquinazolin-4-amine; 1H NMR Spectrum: (DMSO-d6) 1.07 (d, 6H); 1.90 (brs, 1H); 2.80 (m, 1H); 3.83 (s, 2H); 3.97 (s, 3H); 7.20 (s, 1H); 7.28 (t, 1H); 7.50 (m, 2H); 8.32 (s, 1H); 8.43 (s, 1H); 9.76 (s, 1H); Mass Spectrum: (M+H)+ 375.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-d9b9b9bce7e24f82a306b028632cbd9d
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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