Trifluoroacetic acid → HCID 58467980, compound

HRID 1879389Notes

Reaction equation

HRID 1879389 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:19][CH2:18][C@@H:17]([NH:20]C(N2CCC(N3C4C(=NC=CC=4)N(COCC[Si](C)(C)C)C3=O)CC2)=O)[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C@H:10]1[NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C@H:17]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C@@H:10]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])[C@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58468021HCID 58468021, compound

Product 1

HCID 58467980HCID 58467980, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Methylene chloride (1 mL) solution of tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(4-(2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamido)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (12 mg, 0.016 mmol) in TFA (0.5 ml, 6.5 mmol) was stirred at room temperature overnight. The solvent was removed via vacuum and the crude residue was partitioned between ethyl acetate and Sodium bicarbonate (sat). The ethyl acetate layer was separated, dried (sodium sulfate) and concentrated. The desired product was obtained by prep TLC eluting with 10% methanol in methylene chloride:

Workup

  1. customThe solvent was removed via vacuum
  2. customthe crude residue was partitioned between ethyl acetate and Sodium bicarbonate (sat)
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec7d2e01bd094cf98954da589bf4360f
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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