Hydrochloric Acid → HCID 10792343, compound

HRID 1839461Notes

Reaction equation

HRID 1839461 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O.Cl.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:33]([O-:36])([O-])=[O:34].[K+].[K+].[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>O.CO>[CH2:25]([O:36][C:33]([C:15]1[CH:14]=[C:13]([NH:18][C:41](=[O:42])[C:40]2[CH:39]=[CH:43][CH:19]=[C:8]([C:9]#[N:11])[CH:7]=2)[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:19]=[CH:20][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 168937Lithium hydroxide, monohydrateHCID 1133079N-(2-aminophenyl)-4-tert-butylbenzamide

Product 1

HCID 10792343HCID 10792343, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-methoxycarbonyl-N1-(3-cyanobenzoyl)]-N2-(4-t-butylbenzoyl)-1,2-benzenediamine (2.6 g, 5.7 mmol) in THF (80 mL) was added methanol (27 mL), followed by a solution of LiOH.H2O (1 g, 22.8 mmol) in water (27 mL). After 12 h, the pH was adjusted to 3 with conc HCl and the mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with 1 N HCl, brine (2×), MgSO4 dried, and concentrated. To the residue dissolved in DMF (20 mL) was added benzyl bromide (1.06 g, 6.2 mmol), followed by K2CO3 (1.6 g, 11.4 mmol). After 3 h, the reaction was concentrated and the residue was dissolved in ethyl acetate and washed with satd aq NaHCO3 followed by brine. The organic layer was MgSO4 dried and 5 g of silica gel was added. This mixture was concentrated and chromatographed (20% ethyl acetate/hexanes to 60% ethyl acetate/hexanes) to give the title compound as a white solid (1.2 g, 40%); MS(FD): 531.0.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1 N HCl, brine (2×), MgSO4
  4. customdried
  5. concentrationconcentrated
  6. dissolutionTo the residue dissolved in DMF (20 mL)
  7. waitAfter 3 h
  8. concentrationthe reaction was concentrated
  9. dissolutionthe residue was dissolved in ethyl acetate
  10. washwashed with satd aq NaHCO3
  11. customdried
  12. addition5 g of silica gel was added
  13. concentrationThis mixture was concentrated
  14. customchromatographed (20% ethyl acetate/hexanes to 60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f753cd8da62f47bb95642af7ca3a3f96
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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