Trifluoroacetic acid → HCID 70872387, compound

HRID 1616515Notes

Reaction equation

HRID 1616515 reaction equation
[CH2:1]([N:3]([CH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1)[C:4]1[CH:5]=[C:6]([C:26]2[CH:27]=[CH:28][C:29]([N:32]3[CH2:37][CH2:36][CH:35]([NH:38]C(=O)OC(C)(C)C)[CH2:34][CH2:33]3)=[N:30][CH:31]=2)[CH:7]=[C:8]([C:11](=[O:25])[NH:12][CH2:13][C:14]2[C:15](=[O:24])[NH:16][C:17]([CH3:23])=[CH:18][C:19]=2[CH2:20][CH2:21][CH3:22])[C:9]=1[CH3:10])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:38][CH:35]1[CH2:34][CH2:33][N:32]([C:29]2[N:30]=[CH:31][C:26]([C:6]3[CH:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH:46]4[CH2:47][CH2:48][O:49][CH2:50][CH2:51]4)[C:9]([CH3:10])=[C:8]([CH:7]=3)[C:11]([NH:12][CH2:13][C:14]3[C:15](=[O:24])[NH:16][C:17]([CH3:23])=[CH:18][C:19]=3[CH2:20][CH2:21][CH3:22])=[O:25])=[CH:27][CH:28]=2)[CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86684896HCID 86684896, compound

Product 1

HCID 70872387HCID 70872387, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (1-(5-(3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methyl-5-(((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)carbamoyl)phenyl)pyridine-2-yl)piperidin-4-yl)carbamate (0.4 g, 0.00051 mol) in DCM (10 mL) at 0° C., TFA (10 mL) was added and reaction was stirred for 2 h at room temperature. After completion, reaction was concentrated to dryness. The residue was then basified with aqueous sat. bicarbonate solution (80 mL) till pH 8 and aqueous layer extracted with 20% methanol in DCM (60 mL×4). Combined organic phase was dried over Na2SO4 and solvent removed under reduced pressure to afford the title compound (0.315 g, 92.1%) which was used as such for next reaction.

Workup

  1. customreaction
  2. customAfter completion, reaction
  3. concentrationwas concentrated to dryness
  4. extractionextracted with 20% methanol in DCM (60 mL×4)
  5. dry with materialCombined organic phase was dried over Na2SO4 and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-8aff1815c32c4bebb5e61c978613cfa7
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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