Trifluoroacetic acid → HCID 17958697, compound

HRID 2217269Notes

Reaction equation

HRID 2217269 reaction equation
FC(F)(F)C(O)=O.CC(C)(OC([N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:27]=3)[NH:22][C:21]2=[O:37])[CH2:16][CH2:15]1)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:36][N:33]1[CH2:32][CH2:31][N:30]([C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:37])[N:20]([CH:17]2[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]2)[CH2:29]3)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 17958696HCID 17958696, compound

Product 1

HCID 17958697HCID 17958697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

2 mL of trifluoroacetic acid were added to the ice-cooled solution of 1.1 g (2.561 mmol) of 3,4-dihydro-3-[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]-6-(4-methyl-1-piperazinyl)-2(1H)-quinazolinone in 20 mL of methylene chloride. The reaction mixture was stirred for 15 hours at ambient temperature and for 5 hours at 40° C. and then evaporated down in vacuo. The residue remaining was taken up in 5 mL of water, the solution formed was saturated with potassium carbonate and extracted exhaustively with dichloromethane. The combined extracts were evaporated down in vacuo. The residue obtained was purified by column chromatography on silica gel using dichloromethane/methanol 9/1 (v/v) to start with, then dichloromethane/methanol/concentrated ammonia 70/30/3 (v/v/v) as eluant. The appropriate fractions were evaporated down in vacuo, the residue remaining (0.5 g; 59% of theoretical) was used in the next step without further purification.

Workup

  1. customevaporated down in vacuo
  2. customthe solution formed
  3. extractionextracted exhaustively with dichloromethane
  4. customThe combined extracts were evaporated down in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography on silica gel
  7. customThe appropriate fractions were evaporated down in vacuo
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-00f03940d88d4d19903f8bc62e802cc8
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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