4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde → 1-(Tert-butoxycarbonyl)-3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-3-carboxylic acid

HRID 1867754Notes

Reaction equation

HRID 1867754 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:16]=O)[CH:14]=2)[N:9]=[CH:8][N:7]=1.[NH2:24][C:25]1([C:38]([OH:40])=[O:39])[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]1>>[C:34]([O:33][C:31]([N:27]1[CH2:28][CH2:29][CH2:30][C:25]([NH:24][CH2:16][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][C:12]=2[O:18][CH3:19])[N:9]=[CH:8][N:7]=[C:6]3[NH:5][C:4]2[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[C:3]=2[F:23])([C:38]([OH:40])=[O:39])[CH2:26]1)=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

3

Reactant 2

HCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehydeHCID 247296423-Amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

Product 1

HCID 690457921-(Tert-butoxycarbonyl)-3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-3-carboxylic acid

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with 3-amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (Isomer 1) using an analogous method to that described for the equivalent step in Example 1 to give 1-(tert-butoxycarbonyl)-3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-3-carboxylic acid (Isomer 1); 1H NMR Spectrum: (DMSO d6+d4 AcOH) 1.27 (s, 9H); 1.46 (m, 1H); 1.92 (m, 3H); 3.08 (m, 1H); 3.52 (m, 2H); 3.72 (m, 2H); 3.86 (d, 1H); 3.96 (s, 3H); 7.19 (s, 1H); 7.28 (dt, 1H); 7.48 (t, 1H); 7.56 (m, 1H); 8.31 (s, 1H); 8.43 (s, 1H). Mass Spectrum: (M+H)+ 560.5.

Sources & evidence

ORD record
ord-158fc2a8a5f943d4875fcdce1e50f707
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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