Ethyl Acetate → PF-514273

HRID 859200Notes

Reaction equation

HRID 859200 reaction equation
[F:1][C:2]([F:31])([CH3:30])[CH2:3][N:4]([CH2:27][CH2:28][OH:29])[C:5]([C:7]1[C:11](O)=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:8]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[N:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:8]=[C:7]3[C:11]=2[O:29][CH2:28][CH2:27][N:4]([CH2:3][C:2]([F:1])([F:31])[CH3:30])[C:5]3=[O:6])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58763944HCID 58763944, compound

Product 1

HCID 11316919PF-514273

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)4-hydroxy-1H-pyrazole-3-carboxylic acid (2,2-difluoro-propyl)-(2-hydroxy-ethyl)-amide I-3d (10 g, 21 mmol), triphenyl phosphine (8.4 g, 31.5 mmol) in toluene (210 ml) was added 1,1′-(azodicarbonyl)dipiperidine (8.0 g, 31.5 mmol). After 18 hours, 20% ethyl acetate:hexanes (210 ml) was added, the mixture was stirred at ambient temperature for 1 hour and filtered. The filtrate was concentrated in vacuo and the resulting oil was chromatographed on silica gel (20–70% ethyl acetate:hexanes) to afford the title compound (2A-1) as a solid, 7.8 g. 1H NMR in CDCl3 (ppm) δ 7.53–7.50 (m, 1H), 7.38–7.33 (m, 3H), 7.24–7.21 (m, 2H), 7.16–7.13 (m, 2H), 4.45 (br s, 2H), 4.02 (t, 2H), 3.90 (br s, 2H), 1.69 (t, 3H); ms (LCMS) m/z=452.2 (M+1). Combustion analysis calculated for: C: 55.77%; H: 3.79%; N: 9.29%. Found: C: 55.69%; H: 3.52%; N: 9.13%.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting oil was chromatographed on silica gel (20–70% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-3cf9a6b7123f4deaa2362552e9a9cc19
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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