Trifluoroacetic acid → HCID 67971684, compound

HRID 1804635Notes

Reaction equation

HRID 1804635 reaction equation
[CH3:1][C@@H:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67986528tert-butyl (3S)-3-methyl-4-(pyridin-2-ylmethyl)piperazine-1-carboxylate

Product 1

HCID 67971684HCID 67971684, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from step A (320 mg, 1.1 mmol) in DCM (5 ml) was added TFA (2.1 ml, 27.5 mmol) and the resulting mixture stirred at RT for 4 h. Mixture evaporated and residue dissolved in MeOH and passed through an SCX cartridge (eluting with 2M ammonia in methanol) to form free base. Evaporated and residue lypholized from CH3CN/water to afford the title compound 44 mg (21%) as an orange oil. 1H NMR (CDCl3): 1.14 (d, J 6.2 Hz, 3H), 2.24 (m, 1H), 2.47 (m, 1H), 2.64 (dd, J 12.3 and 9.3 Hz, 1H), 2.73 (m, 1H), 2.87-2.97 (m, 3H), 3.44 (d, J 14.2 Hz, 1H), 4.14 (d, J 14.3 Hz, 1H), 7.17 (dd, J 7.0 and 5.4, 1H), 7.47 (d, J 7.8, 1H), 7.66 (m, 1H), 8.56 (d, J 4.7 Hz, 1H).

Workup

  1. customMixture evaporated
  2. dissolutionresidue dissolved in MeOH
  3. washpassed through an SCX cartridge (eluting with 2M ammonia in methanol)
  4. customto form free base
  5. customEvaporated

Sources & evidence

ORD record
ord-7f8d9e9c42eb46e6b5dd7e567fe40ca1
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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