Trifluoroacetic acid → HCID 86726706, compound

HRID 1499460Notes

Reaction equation

HRID 1499460 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:14]=[C:13]([C:15]([NH:17][C:18]2[C:19]([N:27]3[CH2:32][CH2:31][CH2:30][C@H:29]([NH:33]C(=O)OC(C)(C)C)[CH2:28]3)=[C:20]3[CH2:26][CH2:25][CH2:24][C:21]3=[N:22][CH:23]=2)=[O:16])[CH:12]=[CH:11][C:10]=1[F:41].C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.[NH4+].[OH-]>[NH2:33][C@H:29]1[CH2:30][CH2:31][CH2:32][N:27]([C:19]2[C:18]([NH:17][C:15]([C:13]3[CH:12]=[CH:11][C:10]([F:41])=[C:9]([C:3]4[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[N:14]=3)=[O:16])=[CH:23][N:22]=[C:21]3[CH2:24][CH2:25][CH2:26][C:20]=23)[CH2:28]1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726705HCID 86726705, compound

Product 1

HCID 86726706HCID 86726706, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of tert-butyl {(3S)-1-[3-({[6-(2,6-difluorophenyl)-5-fluoropyridin-2-yl]carbonyl}amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]piperidin-3-yl}carbamate (4.0 mg, 0.0070 mmol) in DCM (0.02 mL) was treated with TFA (0.03 mL, 0.4 mmol). The resulting reaction mixture was stirred at room temperature for 30 min. and then concentrated to give a residue, which was diluted with MeOH and neutralized with small amount of NH4OH. After filtration, the crude was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to afford the title compound (2.2 mg, 67%). LCMS calc. for C25H25F3N5O (M+H)+: m/z=468.2. Found: 468.1.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. customto give a residue, which
  4. filtrationAfter filtration
  5. customthe crude was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min.
  6. washeluting with a gradient of MeCN and water with 0.15% NH4OH)

Sources & evidence

ORD record
ord-3b0d01c046344df989f62bdbd525f91e
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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