Trifluoroacetic anhydride → HCID 58109410, compound

HRID 2037465Notes

Reaction equation

HRID 2037465 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][C:32]([NH2:34])=O)([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:35])[CH3:16])=[CH:11][CH:10]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl.CCN(C(C)C)C(C)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][C:32]#[N:34])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:35])[CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 53473394HCID 53473394, compound

Product 1

HCID 58109410HCID 58109410, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 3-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl) propanamide (80 mg, 0.166 mmol) in anhydrous CH2Cl2 (5 mL) and DIEA (0.5 mL) was added TFAA (72 mg, 0.332 mmol) at 0° C. The mixture was stirred for 2 h. The solvent was removed under reduced pressure, and the residue was purified by preparative HPLC to afford 3-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl) propanenitrile (40 mg, yield 54%). 1H NMR (CDCl3): 1.98-2.18 (m, 1H), 2.11-2.40 (m, 4H), 2.51-2.60 (m, 1H), 2.92 (m, 1H), 5.53 (m, 1H), 6.80-6.90 (m, 2H), 6.94 (m, 2H), 7.01 (m, 2H), 7.19 (m, 2H), 7.21 (m, 2H). LC-MS Method 3 tR=1.22 min, m/z=488.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3d345dec48014c86bad1f0c2bd85798f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…