Trichloroacetonitrile → HCID 86685888, compound

HRID 1629794Notes

Reaction equation

HRID 1629794 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(C#N)(Cl)(Cl)Cl.[NH2:41][C@@:42]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:70])([F:69])[F:68])=[CH:59][CH:58]=1)([C:53]([F:56])([F:55])[F:54])[CH2:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=1)=[O:45]>C(Cl)Cl.N1C=CC=CC=1>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]([NH:41][C@:42]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:68])([F:69])[F:70])=[CH:59][CH:58]=1)([CH2:43][C:44](=[O:45])[C:46]1[CH:47]=[CH:48][C:49]([CH3:52])=[CH:50][CH:51]=1)[C:53]([F:56])([F:55])[F:54])=[O:15]

Participants

7

Reactant 4

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 20825N-PhthaloylglycineHCID 86685849(S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(4,4,4-trifluorobutoxy)phenyl)-butan-1-one

Product 1

HCID 86685888HCID 86685888, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-(1,3-dioxoisoindolin-2-yl)acetic acid (592 mg, 2.88 mmol) in dry DCM (10 mL) was added PPh3 (2269 mg, 8.65 mmol) fairy rapidly, and then CCl3CN (500 mg, 3.46 mmol) was added dropwise. The mixture was stirred at rt for 3 h and a solution of Intermediate 2F, isomer 2 (500 mg, 1.15 mmol) in dry DCM (3 mL), followed by pyridine (0.3 mL) were added. The mixture was stirred at rt overnight. The mixture was diluted with DCM (10 mL) and washed with sat'd NaHCO3 (2×8 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography to yield the desired product (620 mg, 87%). LCMS Anal. Calc'd for C31H26F6N2O5 620.17, found [M+H] 621.3.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at rt overnight
  3. washwashed with sat'd NaHCO3 (2×8 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5dd3dbb87b6a447099c954a5be7eb6ad
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

Loading…