Potassium Carbonate → HCID 58243370, compound

HRID 2361682Notes

Reaction equation

HRID 2361682 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].CS(O[CH:20]1[CH2:23][N:22]([C:24]([N:26]2[CH2:32][CH2:31][CH2:30][N:29]([CH:33]3[CH2:36][CH2:35][CH2:34]3)[CH2:28][CH2:27]2)=[O:25])[CH2:21]1)(=O)=O>CN(C=O)C.ClCCl>[CH:33]1([N:29]2[CH2:30][CH2:31][CH2:32][N:26]([C:24]([N:22]3[CH2:23][CH:20]([O:1][C:2]4[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=4)[CH2:21]3)=[O:25])[CH2:27][CH2:28]2)[CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 58243380HCID 58243380, compound

Product 1

HCID 58243370HCID 58243370, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

3-Hydroxy-6-methylpyridine (24 mg, 0.22 mmol) and K2CO3 (33 mg, 0.24 mmol) were stirred in DMF (1 ml) for 30 minutes and 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl methanesulfonate (66 mg, 0.20) was added. The reaction was stirred at 90° C. for 3 days and then diluted with dichloromethane (30 ml) and washed with saturated NaHCO3 (3×15 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1) to give the title product as off-white solid (24 mg, 35%).

Workup

  1. washwashed with saturated NaHCO3 (3×15 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1)

Sources & evidence

ORD record
ord-356e8fc135a7448b8e63807d9d834cfc
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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