Trifluoroacetic acid → HCID 178507782, compound

HRID 2370849Notes

Reaction equation

HRID 2370849 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:13]([NH:21][C:22]([C:24]2[CH:25]=[C:26]([NH:31]C(=O)OC(C)(C)C)[C:27]([OH:30])=[N:28][CH:29]=2)=[O:23])[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].C(O)(C(F)(F)F)=O.CCOC(C)=O>C(Cl)Cl.CCCCCC>[NH2:31][C:26]1[C:27]([OH:30])=[N:28][CH:29]=[C:24]([CH:25]=1)[C:22]([NH:21][C@@H:13]([C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[C:2]([F:1])[CH:3]=1)[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:23]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 178452810HCID 178452810, compound

Product 1

HCID 178507782HCID 178507782, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirred mixture of ((S)-tert-butyl (5-(((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)-2-hydroxypyridin-3-yl)carbamate (600 mg, 0.0011 mol), in DCM (6 mL) was added TFA (1.2 mL, 0.143 mol, Aldrich). The resulting mixture was then stirred for 2 h at room temperature. After completion of the reaction (monitored by TLC, 30% EtOAc in hexane), the reaction mixture was quenched with sat'd NaHCO3 solution (50 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 9.78 (s., 1H), 9.00 (d, J=7.8 Hz, 1H), 8.44 (d, J=4.8 Hz, 1H), 8.13 (d, J=1.8 Hz, 1H), 7.79 (dd, J=1.2, 9.9 Hz, 1H), 7.60-7.43 (m, 3H), 7.35 (d, 8.7 Hz, 1H), 7.26 (d, J=1.8 Hz, 1H), 6.66 (d, J=7.8 Hz, 1H), 6.18 (br.s., 2H). MS (ESI, positive ion) m/z: 441.1 (M+H).

Workup

  1. customthe reaction mixture was quenched with sat'd NaHCO3 solution (50 mL)
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e460e23e79d54bd0aade0fe21bb69c91
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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