Trifluoroacetic acid → HCID 59682929, compound

HRID 1668695Notes

Reaction equation

HRID 1668695 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([C:19]([O:25][C:26]4[CH:34]=[C:33]5[C:29]([CH:30]=[C:31]([CH3:35])[NH:32]5)=[CH:28][CH:27]=4)=[N:20][CH:21]=[N:22]3)=[CH:17][C:16]=2[O:36][CH3:37])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:37][O:36][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[N:22]=[CH:21][N:20]=[C:19]2[O:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[C:31]([CH3:35])[NH:32]2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59682905HCID 59682905, compound

Product 1

HCID 59682929HCID 59682929, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-{[1-(tert-Butoxycarbonyl)-piperidin-4-yl]oxy}-6-methoxy-4-[(2-methyl-1H-indol-6-yl)oxy]quinazoline (1 g) was dissolved in dichloromethane (5 ml) and cooled in an ice bath. TFA (2.5 ml) was added and the reaction mixture stirred at this temperature for 35 minutes. The volatiles were removed by filtration and the residue taken up into ice cold water. The pH was adjusted to 12 with sodium hydroxide 2N and extracted twice with dichloromethane. The combined extracts were washed in turn with water and brine and dried over magnesium sulphate and the solvent evaporated under vacuum to give 6-methoxy-4-[(2-methyl-1H-indol-6-yl)oxy]-7-[(piperidin-4-yl)oxy]quinazoline (0.765 g) as a solid foam.

Workup

  1. temperaturecooled in an ice bath
  2. customThe volatiles were removed by filtration
  3. extractionextracted twice with dichloromethane
  4. washThe combined extracts were washed in turn with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-129d1c90312a4c44b2286e3d423e330c
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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