Pyridine → HCID 22278713, compound

HRID 1063267Notes

Reaction equation

HRID 1063267 reaction equation
[CH2:1]([C:3]1[C:4]([NH:23][CH:24]([CH3:28])[CH2:25][CH2:26][OH:27])=[N:5][C:6]([CH2:21][CH3:22])=[C:7]([C:9]2[C:18]([O:19][CH3:20])=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH:10]=2)[N:8]=1)[CH3:2].N1C=CC=CC=1.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[C:35]([O:27][CH2:26][CH2:25][CH:24]([NH:23][C:4]1[C:3]([CH2:1][CH3:2])=[N:8][C:7]([C:9]2[C:18]([O:19][CH3:20])=[CH:17][C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[CH:10]=2)=[C:6]([CH2:21][CH3:22])[N:5]=1)[CH3:28])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22278698HCID 22278698, compound

Product 1

HCID 22278713HCID 22278713, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL dry round bottom flask equipped with a magnetic stir bar was charged with a solution of 3-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}butan-1-ol (Example 39, 192 mg, 0.5 mmol) in CH2Cl2 (5 mL). The reaction was cooled with an ice bath and then treated with pyridine (0.044 mL, 0.55 mmol) followed by acetyl chloride (0.039 mL, 0.55 mmol). The solution turned from clear to a light yellow. The ice bath was removed and the reaction was stirred at ambient temperature for 2 hours. The reaction was diluted with CH2Cl2, washed twice with water, once with brine, dried with MgSO4, filtered and concentrated to give 217 mg of a crude oil. This material was purified by Biotage MPLC (40 g column, 20% ethyl acetate in heptane) to give 208 mg (97%) of 3-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}butyl acetate as a clear oil. Rf 0.15 (5% acetone in toluene). OAMS supporting ions at: ESI+ 426.1.

Workup

  1. customA 25 mL dry round bottom flask
  2. customequipped with a magnetic stir bar
  3. temperatureThe reaction was cooled with an ice bath
  4. customThe ice bath was removed
  5. additionThe reaction was diluted with CH2Cl2
  6. washwashed twice with water, once with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 217 mg of a crude oil
  11. customThis material was purified by Biotage MPLC (40 g column, 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-105e317252e3462e83642ae5fdce8d1d
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

Loading…