Trifluoroacetic acid → HCID 86679139, compound

HRID 1774765Notes

Reaction equation

HRID 1774765 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([CH2:14][N:13]([C:15]3[CH:20]=[N:19][CH:18]=[C:17]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]([CH3:31])[C:26](=[O:32])[CH2:25][CH2:24]5)[N:16]=3)[CH2:12]2)[CH2:9]1)=O)(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH2:12]1[C:10]2([CH2:9][NH:8][CH2:11]2)[CH2:14][N:13]1[C:15]1[N:16]=[C:17]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[C:26](=[O:32])[CH2:25][CH2:24]3)[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71533393HCID 71533393, compound

Product 1

HCID 86679139HCID 86679139, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[6-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyrazin-2-yl]-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (example 28, 0.231 g, 0.53 mmol) in DCM (3 mL) was added TFA (0.605 g, 5.3 mmol) and the reaction mixture was stirred at room temperature over night. The mixture was evaporated several times with toluene and then the residue was purified by reverse phase HPLC on a Gemini-NX column, eluting with a 20 to 98% MeOH—H2O (0.05% TEA) gradient to give the title compound (0.203 g, 99%) as a yellow solid (TFA salt). MS: 336.3 (M+H+).

Workup

  1. customThe mixture was evaporated several times with toluene
  2. customthe residue was purified by reverse phase HPLC on a Gemini-NX column
  3. washeluting with a 20 to 98% MeOH—H2O (0.05% TEA) gradient

Sources & evidence

ORD record
ord-d8e36c73324c4698a14690415d8a9c27
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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