Tetrahydrofuran → HCID 178452810, compound

HRID 2370848Notes

Reaction equation

HRID 2370848 reaction equation
C([C:5]1[C:6]([O:34]CC2C=CC=CC=2)=[N:7][CH:8]=[C:9]([C:11](=[O:33])[NH:12][C@@H:13]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[C:23]([F:32])[CH:22]=2)[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:10]=1)(C)(C)C.[C:42](=[O:45])([O-:44])[NH2:43].[H][H].[CH3:48]COC(C)=O.[CH2:54]1[CH2:58]OC[CH2:55]1>[Pd]>[F:32][C:23]1[CH:22]=[C:21]([C@H:13]([NH:12][C:11]([C:9]2[CH:10]=[C:5]([NH:43][C:42](=[O:44])[O:45][C:54]([CH3:55])([CH3:58])[CH3:48])[C:6]([OH:34])=[N:7][CH:8]=2)=[O:33])[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:26]=[CH:25][C:24]=1[O:27][C:28]([F:30])([F:31])[F:29]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 86687992HCID 86687992, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178452810HCID 178452810, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred mixture of (S)-tert-butyl (2-(benzyloxy)-5-(((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)pyridine)-carbamate (800 mg, 0.0012 mol) in THF (8 mL) was added 10% Pd/C (800 mg, Aldrich). The reaction mixture was stirred under a hydrogen atmosphere in the form of a hydrogen bladder (˜20-22 PSI) for 12 h at room temperature. After completion of the reaction (monitored by TLC, 100% EtOAc), the reaction mixture was filtered through Celite® brand filter agent. The filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 10.40 (br. s., 1H), 9.42 (d, J=7.8 Hz, 1H), 9.01 (s, 1H), 8.45 (d, J=4.8 Hz, 1H), 8.35 (d, J=1.8 Hz, 1H), 7.95 (s, 1H), 7.80 (t, 9.6 Hz, 1H), 7.61-7.45 (m, 4H), 7.37 (d, 8.4 Hz, 1H), 1.44 (s, 9H). MS (ESI, positive ion) m/z: 541 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered through Celite® brand
  2. filtrationfilter agent
  3. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81bf9c1d492c4529878e22d98d7a541a
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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