1-Naphthoyl fluoride → 3-(3-{3-t-Butyl-5-[(naphthalene-1-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

HRID 1392311Notes

Reaction equation

HRID 1392311 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH2:18])=[CH:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)[CH:8]=1)[CH3:2].[C:24]1([C:34](F)=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:34]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)=[O:35])=[CH:16][C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14]2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2632231-Naphthoyl fluorideHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

Product 1

HCID 588428683-(3-{3-t-Butyl-5-[(naphthalene-1-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl esterYield 372.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example Z (315 mg, 1.0 mmol) and Barton's base (0.5 mL) in anhydrous CH2Cl2 (5 mL) under N2 was stirred at RT for 30 min, and then added to a solution of naphthalene-1-carbonyl fluoride (348 mg, 0.2 mmol) in anhydrous CH2Cl2 (5 mL). The resulting mixture was stirred at RT overnight. After quenching with water (100 mL), the reaction mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried (NaSO4), filtered and concentrated under reduced pressure to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[(naphthalene-1-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester, (350 mg, 74%). 1H-NMR (CDCL3): 8.29 (d, J=8.0 Hz, 1H), 7.98 (d, J=7.2 Hz, 2H), 7.89 (d, J=7.2 Hz, 1H), 7.62-7.57 (m, 3H), 7.49-7.28 (m, 4H), 7.03 (s, 1H), 3.94 (q, J=7.2 Hz, 2H), 2.96 (t, J=7.2 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.45 (s, 9H), 1.13 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 470 (M+H+).

Workup

  1. customAfter quenching with water (100 mL)
  2. extractionthe reaction mixture was extracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a residue which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3d5e7a3ce6cf4c00b09dd412c08ba45b
Source dataset
uspto-grants-2008_03
Patent number
US07342037B2

Reaction notes

Loading…