Acetic Acid → HCID 18506846, compound

HRID 1355478Notes

Reaction equation

HRID 1355478 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=1)(=O)[CH3:2].[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].CC(O)=O.[BH3-]C#N.[Na+]>CO.C([O-])(O)=O.[Na+]>[C:18]([N:21]1[CH2:26][CH2:25][N:24]([CH:1]([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=2)[CH3:2])[CH2:23][CH2:22]1)(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 837951-AcetylpiperazineHCID 5003444Sodium cyanoborohydride2×HCID 18506796HCID 18506796, compound

Product 1

HCID 18506846HCID 18506846, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of tert-butyl 4-acetylpyridin-2-ylcarbamate (16-3, 187 mg, 0.79 mmole) in MeOH (3 mL) was added 1-acetylpiperazine (304 mg, 2.37 mmole), glacial HOAc (0.14 mL, 2.3.7 mmole), and NaBH3CN (149 mg, 2.37 mmole) then the mixture was heated to 50° C. After 6 hr additional NaBH3CN (149 mg, 2.37 mmole) was added and heating continued. After 18 hr the mixture was cooled to RT, diluted with saturated NaHCO3, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 0-10% EtOH/EtOAc) gave the titled compound as an oil: 1H-NMR (500 MHz, CDCl3) δ8.17 (d, 1H, J=5.13 Hz), 7.87 (s, 1H), 7.52 (bs, 1H), 6.97 (d, 1H, J=5.13 Hz), 3.64-3.57 (m, 2H), 3.45-3.39 (m, 3H), 2.49-2.35 (m, 4H), 2.06 (s, 3H) 1.54 (s, 9H), 1.35 (d, 3H, J=6.59 Hz).

Workup

  1. temperatureheating
  2. temperatureAfter 18 hr the mixture was cooled to RT
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f550941803f1405983cbd022ab9da8e2
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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