Trifluoroacetic acid → HCID 22248819, compound

HRID 890567Notes

Reaction equation

HRID 890567 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]([O:20][CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[CH3:22])[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH:21]([O:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:19]=1)[CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69596297HCID 69596297, compound

Product 1

HCID 22248819HCID 22248819, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[1-(2-chloro-phenyl)-ethoxy]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (I-2b) (64.3 mg, 0.15 mmol) in 2.0 mL of dichloromethane was added trifluoroacetic acid (177.4 μL, 2.30 mmol) and the mixture was stirred for 1.5 h at ambient temperature. The reaction was concentrated, and the residue dissolved in 1 M HCl(aq) (10 mL). This was extracted with ethyl acetate (10 mL), separated, and the aqueous layer was adjusted to a pH of 12 using 5 M KOH(aq). This aqueous mixture was extracted with ethyl acetate (2×15 mL) and the combined organic extracts were dried over sodium sulfate and concentrated to give 58.2 mg of the title product (2-A).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue dissolved in 1 M HCl(aq) (10 mL)
  3. extractionThis was extracted with ethyl acetate (10 mL)
  4. customseparated
  5. extractionThis aqueous mixture was extracted with ethyl acetate (2×15 mL)
  6. dry with materialthe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff2c4bc2b8be4f188e396a1a132a7919
Source dataset
uspto-grants-2006_02
Patent number
US06995159B2

Reaction notes

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