Trifluoroacetic acid → HCID 22030922, compound

HRID 454189Notes

Reaction equation

HRID 454189 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7]=[C:6]2[O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28][CH2:27]2.C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7]=[C:6]2[O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH2:29][CH2:28][CH2:27]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22030734HCID 22030734, compound

Product 1

HCID 22030922HCID 22030922, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-methoxy-7-(3-morpholinopropoxy)-4-((1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)oxy)quinazoline (110 mg, 0.2 mmol) in solution in dichloromethane (3 ml) was added TFA (0.3 ml) and the mixture stirred for 1 hour at ambient temperature. The solvents were evaporated and the remaining oil was diluted with dichloromethane and the pH adjusted to 9 with a saturated solution of sodium hydrogen carbonate. The organic phase was washed with, brine, dried (MgSO4), filtered and the solvent evaporated to give 6-methoxy-7-(3-morpholinopropoxy)-4-(1,2,3,4-tetrahydroquinolin-6-yloxy)quinazoline (84 mg, 93%).

Workup

  1. customThe solvents were evaporated
  2. additionthe remaining oil was diluted with dichloromethane
  3. washThe organic phase was washed with, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-5733ebc89b2c48c98e6102c2636229c1
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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