Trifluoroacetic acid → HCID 59682923, compound

HRID 1668691Notes

Reaction equation

HRID 1668691 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][O:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28]([O:34][C:35]4[CH:36]=[C:37]5[C:41](=[CH:42][CH:43]=4)[NH:40][C:39]([CH3:44])=[CH:38]5)=[N:29][CH:30]=[N:31]3)=[CH:26][C:25]=2[O:45][CH3:46])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:46][O:45][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:24]=1[O:23][CH2:22][CH2:21][N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1)[N:31]=[CH:30][N:29]=[C:28]2[O:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][C:39]([CH3:44])=[CH:38]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59682921HCID 59682921, compound

Product 1

HCID 59682923HCID 59682923, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (8 ml) was added to a solution of 7-{2-[4-(tert-butoxycarbonyl)piperazin-1-yl]ethoxy}-6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline (2.75 g) in dichloromethane (30 ml) at 0° C. and the reaction mixture was stirred at this temperature for 1 hour before being concentrated in vacuum in a cold bath (˜20° C.). Cold water was added to the residue and the pH was adjusted to 10.5 with 1N sodium hydroxide. After several extractions with dichloromethane, the combined organic layers were dried over magnesium sulphate, filtered and concentrated in vacuum to give 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-(piperazin-1-yl)ethoxy]quinazoline (1.8 g) as a white solid.

Workup

  1. concentrationbefore being concentrated in vacuum in a cold bath (˜20° C.)
  2. additionCold water was added to the residue
  3. extractionAfter several extractions with dichloromethane
  4. dry with materialthe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-800ee8d3d46e493dabb422d047a5d898
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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