HCID 58043125, compound → HCID 66653686, compound

HRID 1035193Notes

Reaction equation

HRID 1035193 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][CH:10]2[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[CH:7][C:6]=1[F:23])[CH3:3]>Cl.CO>[NH:12]1[CH2:13][CH:10]([O:9][C:8]2[CH:21]=[CH:22][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[C:6]([F:23])[CH:7]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 58043125HCID 58043125, compound

Product 1

HCID 66653686HCID 66653686, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Intermediate 26B (1.2 g, 3.7 mmol) was dissolved in a 4.0 M solution of HCl in MeOH (20 mL) and the reaction mixture was stirred at RT over for four hours. The mixture was concentrated and the residue was dissolved in water. The aqueous solution was basified to pH=10 with aqueous NaOH (1.0 M) and extracted with DCM (4×30 mL). The combined organic phases were filtered through a phase separator and the solvent was removed by evaporation. There was obtained 0.71 g (86%) of 26C as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 2.24 (s, 6H), 3.41 (s, 2H), 3.73-3.83 (m, 2H), 3.87-3.97 (m, 2H), 4.90-5.02 (m, 1H), 6.41-6.55 (m, 2H), 7.16-7.24 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with DCM (4×30 mL)
  4. filtrationThe combined organic phases were filtered through a phase separator
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-fa7050ce3b1e49fb9ed1abb01b8af082
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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