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

HRID 1867680Notes

Reaction equation

HRID 1867680 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][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1>>[C:34]([O:33][C:31]([N:28]1[CH2:27][CH2:26][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])[CH2:30][CH2:29]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

3

Reactant 2

HCID 6937974-Amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acidHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 690480781-(Tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-4-carboxylic acid

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with 4-amino-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid using an analogous method to that described for the equivalent step in Example 1 to give 1-(tert-butoxycarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidine-4-carboxylic acid; 1H NMR Spectrum: (DMSO d6) 1.39 (s, 9H); 1.70 (m, 2H); 1.86 (m, 2H); 3.43 (m, 4H); 3.76 (s, 2H); 3.96 (s, 3H); 7.19 (s, 1H); 7.28 (t, 1H); 7.48 (t, 1H); 7.55 (t, 1H); 8.37 (s, 1H); 8.43 (s, 1H); 9.78 (s, 1H); Mass Spectrum: (M+H)+ 560.

Sources & evidence

ORD record
ord-2048e33d1d574332b4a1733e6d746699
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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