Hydrochloric Acid → HCID 59277595, compound

HRID 2097212Notes

Reaction equation

HRID 2097212 reaction equation
[C:1]([C:3]1[C:4]([NH:9][C@@H:10]([CH3:16])[C:11](OCC)=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].C[O-].[Na+].Cl>CO.[Ni]>[CH3:16][C@@H:10]1[NH:9][C:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][NH:2][C:11]1=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 59277585HCID 59277585, compound

Product 1

HCID 59277595HCID 59277595, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-ethyl 2-(3-cyanopyridin-2-ylamino)propanoate (720 mg, 3.28 mmol) in methanol (10 mL) and sodium methoxide (3.28 mmol) is added a pinch of Raney nickel and the reaction was stirred under hydrogen for 6 h. Once the reaction was complete, 1 eq of HCl was added and the solution filtered through celite, and washed with methanol. The solution was concentrated and re-solvated in ethyl acetate (10 mL) and washed with water (20 mL), the organic layers were combined, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to yield a white solid (136 mg, 23%): 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.32 (s, 1H), 6.60-6.57 (m, 1H), 4.99 (d, J=16.4 Hz, 1H), 4.12-4.10 (m, 1H), 3.87 (d, J=16.4 Hz, 1H), 1.38 (d, J=6.8 Hz, 3H).

Workup

  1. filtrationthe solution filtered through celite
  2. washwashed with methanol
  3. concentrationThe solution was concentrated and re-solvated in ethyl acetate (10 mL)
  4. washwashed with water (20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-72463e9345f640d19bd1b35033f80ad4
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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