3-Chloro-2-fluoroaniline → HCID 58318650, compound

HRID 1027936Notes

Reaction equation

HRID 1027936 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:30][CH3:31])=[C:9]([O:12][C@H:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[C@@H:15]([C:26]([O:28][CH3:29])=[O:27])[CH2:14]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:32][C:33]1[C:34]([F:40])=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36]>>[Cl:32][C:33]1[C:34]([F:40])=[C:35]([NH:36][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:30][CH3:31])=[C:9]([O:12][C@H:13]4[CH2:18][CH2:17][NH:16][C@@H:15]([C:26]([O:28][CH3:29])=[O:27])[CH2:14]4)[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 750143-Chloro-2-fluoroanilineHCID 58318653HCID 58318653, compound

Product 1

HCID 58318650HCID 58318650, compound

Procedure

1-tert-butyl 2-methyl (2R,4S)-4-[(4-chloro-7-methoxyquinazolin-6-yl)oxy]piperidine-1,2-dicarboxylate (17) was reacted with 3-Chloro-2-fluoroaniline analogously as for the equivalent step in Example 7 to give methyl (2R,4S)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)piperidine-2-carboxylate (18): 1H NMR Spectrum: (DMSO-d6) δ1.45-1.56 (2H, m), 2.03-2.12 (1H, m), 2.31-2.38 (1H, m), 2.60-2.67 (1H, m), 3.08-3.15 (1H, m), 3.44-3.48 (1H, m), 3.64 (3H, s), 3.95 (3H, s), 4.55-4.63 (1H, m), 7.23 (1H, s), 7.26-7.32 (1H, m), 7.48-7.58 (2H, m), 7.85 (1H, s), 8.38 (1H, s), 9.56 (1H, s); Mass Spectrum: (M+H)+ 461.

Sources & evidence

ORD record
ord-4c2f85afced3474797daa8fde86057bb
Source dataset
uspto-grants-2014_05
Patent number
US08735410B2

Reaction notes

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