Trifluoroacetic acid → HCID 71144315, compound

HRID 2370802Notes

Reaction equation

HRID 2370802 reaction equation
[F:1][C:2]1[C:3]([C@@H:8]([NH:19][C:20]([C:22]2[N:27]=[CH:26][C:25]([O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])=[CH:24][CH:23]=2)=[O:21])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[C:3]([C@@H:8]([NH:19][C:20]([C:22]2[N:27]=[CH:26][C:25]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:24][CH:23]=2)=[O:21])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71144003HCID 71144003, compound

Product 1

HCID 71144315HCID 71144315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (S)-tert-butyl 2-((6-(((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)pyridin-3-yl)oxy)acetate from above in DCM (0.5 mL), was added TFA (0.550 mL, 7.40 mmol). The resulting mixture was then stirred at rt for 1 h. The mixture was then concentrated and MeOH (1 mL) was added. The mixture was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the title compound as a white solid. 1H NMR (400 MHz, MeOH) δ ppm 8.55 (d, J=4.7 Hz, 1H), 8.42 (d, J=2.5 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 7.59-7.72 (m, 5H), 7.42-7.55 (m, 2H), 6.68 (d, J=1.6 Hz, 1H), 4.89 (s, 2H). MS (ESI pos. ion) m/z: 450.2 (M+H).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionMeOH (1 mL) was added
  3. customThe mixture was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-f390381972d0458bb2f6531be91e1931
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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