Sodium Hydroxide → HCID 58514251, compound

HRID 1910737Notes

Reaction equation

HRID 1910737 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23]C(=O)C4C=CC=CC=4)[CH:18]=3)[CH:14]=[CH:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+]>Cl.C(Cl)Cl>[NH2:23][C:19]1[CH:18]=[C:17]([C:13]2[CH:12]=[C:11]([C:9](=[O:10])[CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:16]=[CH:15][CH:14]=2)[CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58514117HCID 58514117, compound

Product 1

HCID 58514251HCID 58514251, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

N-{4-[3-(3-Morpholin-4-yl-propionyl)-phenyl]-pyridin-2-yl}-benzamide (100 mg, 0.32 mmol) was dissolved in HCl (2 mL, 6 N). The mixture was irradiated with microwaves at 140° C. for 30 minutes. The mixture was diluted with DCM (20 mL) and neutralized with NaOH to pH 9. The layers were separated and the aqueous layer was washed further with DCM (2×15 mL). The combined organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified to give 1-[3-(2-Amino-pyridin-4-yl)-phenyl]-3-morpholin-4-yl-propan-1-one (TFA salt) as a white solid (84 mg, 78%). MS: m/z 312.3 [MH+].

Workup

  1. customThe mixture was irradiated with microwaves at 140° C. for 30 minutes
  2. customThe layers were separated
  3. washthe aqueous layer was washed further with DCM (2×15 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified

Sources & evidence

ORD record
ord-4289cc1d66104bbd8f9485350d5f2054
Source dataset
uspto-grants-2013_12
Patent number
US08604031B2

Reaction notes

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