Hydrochloric Acid → HCID 57703719, compound

HRID 1632101Notes

Reaction equation

HRID 1632101 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[C:17]([F:31])=[C:18]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:11][N:10]=1)(C)(C)C.Cl>[Pd].CO>[Cl:30][C:26]1[CH:25]=[C:24]([C:18]2[C:19]([O:22][CH3:23])=[CH:20][CH:21]=[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([CH2:8][NH2:7])=[N:10][CH:11]=3)[C:17]=2[F:31])[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68653889HCID 68653889, compound

Product 1

HCID 57703719HCID 57703719, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 100 mL round bottom flask was added P-355 (0.55 g, 1.56 mmol), methanol (20 mL), concentrated HCl (0.65 mL, 7.79 mmol), and 10% Pd/C (100 mg). The suspension was stirred under a H2 balloon for 18 hours, then filtered through Celite. The filtrate was concentrated. To the solid was added 1N aqueous NaOH and the product was extracted with dichloromethane. The dichloromethane was concentrated and purified by flash column chromatography eluting with 5-10% methanol/dichloromethane to give P-344 (89 mg, 16%) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) 8.55 (d, J=1.2 Hz, 1H), 8.32 (br s, 3H), 7.71 (dd, J=1.9, 7.9 Hz, 1H), 7.50-7.37 (m, 3H), 7.36 (d, J=5.4 Hz, 2H), 7.27 (d, J=6.6 Hz, 1H), 6.96 (d, J=8.6 Hz, 1H), 4.75 (br s, 2H), 4.14 (q, J=5.8 Hz, 2H), 4.01 (s, 2H), 3.73 (s, 3H) ppm. LC/MS=95.1%, 357.1 (APCI+).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. additionTo the solid was added 1N aqueous NaOH
  4. extractionthe product was extracted with dichloromethane
  5. concentrationThe dichloromethane was concentrated
  6. custompurified by flash column chromatography
  7. washeluting with 5-10% methanol/dichloromethane
  8. customto give P-344 (89 mg, 16%) as a colorless oil

Sources & evidence

ORD record
ord-4527785cdd7147869eb465fd638bf68e
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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