Trifluoroacetic acid → HCID 118021411, compound

HRID 531316Notes

Reaction equation

HRID 531316 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:64])([F:63])[C:10]1[CH:11]=[C:12]([C@H:20]2[O:24][C:23](=[O:25])[N:22]([CH2:26][C:27]3[C:32]([C:33]4[C:34]([O:54][CH3:55])=[N:35][CH:36]=[C:37]([C:39]5[C:51]([CH3:52])=[CH:50][C:42]([C:43]([O:45]C(C)(C)C)=[O:44])=[CH:41][C:40]=5[CH3:53])[CH:38]=4)=[CH:31][CH:30]=[C:29]([N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[N:28]=3)[C@H:21]2[CH3:62])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>C(Cl)Cl>[F:19][C:16]([F:17])([F:18])[C:14]1[CH:13]=[C:12]([C@H:20]2[O:24][C:23](=[O:25])[N:22]([CH2:26][C:27]3[C:32]([C:33]4[C:34]([O:54][CH3:55])=[N:35][CH:36]=[C:37]([C:39]5[C:40]([CH3:53])=[CH:41][C:42]([C:43]([OH:45])=[O:44])=[CH:50][C:51]=5[CH3:52])[CH:38]=4)=[CH:31][CH:30]=[C:29]([N:56]4[CH2:61][CH2:60][O:59][CH2:58][CH2:57]4)[N:28]=3)[C@H:21]2[CH3:62])[CH:11]=[C:10]([C:9]([F:64])([F:63])[F:8])[CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90009308HCID 90009308, compound

Product 1

HCID 118021411HCID 118021411, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (0.095 mL, 1.240 mmol) and tert-butyl 4-[2′-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-methoxy-6′-(morpholin-4-yl)-3,3′-bipyridin-5-yl]-3,5-dimethylbenzoate (EXAMPLE 55, 44 mg, 0.055 mmol) in CH2Cl2 (0.5 mL) was stirred at room temperature overnight, after which time TLC and LCMS showed the reaction to be complete. After solvent was removed in vacuo, the crude was dissolved in CH3CN and purified by reverse phase HPLC (C18 stationary phase, using a gradient from 10-100% CH3CN/water (modified with 0.05% TFA) to give the titled compound (33 mg, 0.038 mmol, 70% yield) as white solid after lyophilization. LCMS (M+H)+: 731.0. 1H NMR (CD3OD, 500 MHz): δ 8.18 (d, 1H), 7.99 (s, 1H), 7.97 (s, 1H), 7.91 (d, 1H), 7.89 (s, 2H), 7.63 (d, 1H), 7.51 (d, 1H), 7.38 (d, 1H), 6.88 (d, 1H), 5.79 (d, 1H), 4.73 (d, 1H), 4.20-4.31 (m, 1H), 4.03-4.17 (m, 1H), 3.99 (s, 3H), 3.83 (t, 4H), 3.60 (t, 4H), 2.38 (s, 3H), 0.66 (brd, 3H). RTA IC50: 9 nM.

Workup

  1. customthe reaction
  2. customAfter solvent was removed in vacuo
  3. dissolutionthe crude was dissolved in CH3CN
  4. custompurified by reverse phase HPLC (C18 stationary phase

Sources & evidence

ORD record
ord-aaca962856c4431bae8bf445169ab730
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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