Trifluoroacetic acid → N-(4-chloro-2,6-difluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amine

HRID 577386Notes

Reaction equation

HRID 577386 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([NH:26][C:27]4[C:32]([F:33])=[CH:31][C:30]([Cl:34])=[CH:29][C:28]=4[F:35])=[N:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[O:36][CH3:37])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:34][C:30]1[CH:31]=[C:32]([F:33])[C:27]([NH:26][C:20]2[C:19]3[C:24](=[CH:25][C:16]([O:15][CH2:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[C:17]([O:36][CH3:37])[CH:18]=3)[N:23]=[CH:22][N:21]=2)=[C:28]([F:35])[CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 111352807-(1-(Tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazoline

Product 1

HCID 5329050N-(4-chloro-2,6-difluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amineYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using an analogous procedure to that described in Example 9, 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(4-chloro-2,6-difluoroanilino)-6-methoxyquinazoline (95 mg, 0.2 mmol) in methylene chloride (2 ml) was treated with TFA (800 μl) to give 4-(4-chloro-2,6-difluoroanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (20 mg, 26%).

Sources & evidence

ORD record
ord-f1fb942036054bedb846d48cf165e11a
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

Loading…