Trifluoroacetic acid → HCID 86726690, compound

HRID 1499446Notes

Reaction equation

HRID 1499446 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([NH:16][C:17]2[C:18]([N:26]3[CH2:31][CH2:30][CH2:29][C@H:28]([NH:32]C(=O)OC(C)(C)C)[CH2:27]3)=[C:19]3[CH2:25][CH2:24][CH2:23][C:20]3=[N:21][CH:22]=2)=[O:15])[N:13]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.[NH4+].[OH-]>[NH2:32][C@H:28]1[CH2:29][CH2:30][CH2:31][N:26]([C:18]2[C:17]([NH:16][C:14]([C:12]3[N:13]=[C:9]([C:3]4[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[S:10][CH:11]=3)=[O:15])=[CH:22][N:21]=[C:20]3[CH2:23][CH2:24][CH2:25][C:19]=23)[CH2:27]1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726689HCID 86726689, compound

Product 1

HCID 86726690HCID 86726690, compoundYield 59.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

tert-Butyl {(3S)-1-[3-({[2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]piperidin-3-yl}carbamate (4 mg, 0.007 mmol) was dissolved in DCM (0.02 mL) and then TFA (0.03 mL, 0.4 mmol) was added. 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. The mixture was filtered and purified by preparative LC-MS (XBridge™ preparative C18 30×10 mm, 5 m OBD™ column, at flow rate of 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to afford the title compound (1.9 mg, 58%). LCMS calc. for C23H24F2N5OS (M+H)+: m/z=456.2. Found: 456.1.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. customto give a residue, which
  4. filtrationThe mixture was filtered
  5. custompurified by preparative LC-MS (XBridge™ preparative C18 30×10 mm, 5 m OBD™ column
  6. washat flow rate of 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH)

Sources & evidence

ORD record
ord-229bf454784f460c8f244a2446aeebfe
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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