Trifluoroacetic acid → N-(5-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}pentyl)-L-leucine

HRID 1667387Notes

Reaction equation

HRID 1667387 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:32]([F:33])=[CH:31][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C@H:19]([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:10][C:9]=2[F:34])[C:6](=[O:35])[CH:5]=[CH:4][C:3]=1[C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=1[F:44].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]([C:8]2[C:9]([F:34])=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:31][C:32]=2[F:33])[C:6](=[O:35])[CH:5]=[CH:4][C:3]=1[C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=1[F:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57658405HCID 57658405, compound

Product 1

HCID 57658309N-(5-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}pentyl)-L-leucine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

From Example 54. To a solution of tert-butyl N-(5-{4-[6-amino-5-(2,4-difluorobenzoyl)-2-oxopyridin-1(2H)-yl]-3,5-difluorophenoxy}pentyl)-L-leucinate (21 mg, 0.04 mmol) in DCM (2.5 ml) was added TFA (2.5 ml). The mixture was stirred at room temperature for 20 hours, before concentrating under reduced pressure. The residue was dissolved in minimal MeOH and azeotroped with 1:1 toluene/DCM three times. The title compound was afforded as a cream coloured solid as the mono-TFA salt (21 mg, 92% yield).

Workup

  1. concentrationbefore concentrating under reduced pressure
  2. dissolutionThe residue was dissolved in minimal MeOH
  3. customazeotroped with 1:1 toluene/DCM three times

Sources & evidence

ORD record
ord-489157acda554c2db45f0124378e5239
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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