3-(Boc-amino)-L-alanine → 3-[(tert-butoxycarbonyl)amino]-N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-L-alanine

HRID 1867717Notes

Reaction equation

HRID 1867717 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.[C:24]([O:28][C:29]([NH:31][CH2:32][C@@H:33]([C:35]([OH:37])=[O:36])[NH2:34])=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[C:24]([O:28][C:29]([NH:31][CH2:32][C@@H:33]([C:35]([OH:37])=[O:36])[NH:34][CH2:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:18][CH3:19])[N:9]=[CH:8][N:7]=[C:6]2[NH:5][C:4]1[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[C:3]=1[F:23])=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 103528593-(Boc-amino)-L-alanineHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 690487083-[(tert-butoxycarbonyl)amino]-N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-L-alanine

Procedure

4-(3-Chloro-2-fluoroanilino)-7-methoxyquinazoline-6-carbaldehyde was coupled with 3-[(tert-butoxycarbonyl)amino]-L-alanine (Tetrahedron Letters (1993), 34(20), 3201-4) using an analogous method to that described for the equivalent step in Example 1 to give 3-[(tert-butoxycarbonyl)amino]-N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-L-alanine; 1H NMR Spectrum: (DMSO-d6) 1.32 (s, 9H); 3.26 (m, 3H); 3.86 (d, 1H); 3.97 (m, 4H); 6.73 (s, 1H); 7.21 (s, 1H); 7.27 (t, 1H); 7.47 (t, 1H); 7.54 (t, 1H); 8.40 (s, 1H); 8.44 (s, 1H); 9.86 (s, 1H); Mass Spectrum: (M+H)+ 520.

Sources & evidence

ORD record
ord-72a80958c69b4f718a8a7b55c20d3b10
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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