Trifluoroacetic acid → HCID 5329049, compound

HRID 577379Notes

Reaction equation

HRID 577379 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[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[F:34])=[N:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[O:35][CH3:36])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:28]1[CH:29]=[C:30]([CH3:33])[CH:31]=[CH:32][C:27]=1[NH:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([O:15][CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[C:17]([O:35][CH3:36])[CH:18]=2)[N:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 109620857-(1-(Tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(2-fluoro-4-methylanilino)-6-methoxyquinazoline

Product 1

HCID 5329049HCID 5329049, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-4-(2-fluoro-4-methylanilino)-6-methoxyquinazoline (318 mg, 0.64 mmol) in methylene chloride (5 ml) containing TFA (2.5 ml) was stirred at ambient temperature for 2 hours. The volatiles were removed under vacuum and the residue was partitioned between methylene chloride and water. The aqueous layer was adjusted to pH10-11. The organic layer was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation to give 4-(2-fluoro-4-methylanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (220 mg, 87%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-f3c9b9912d2d474b9e1cc9d9cdfe844f
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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