Pyridine → HCID 18009537, compound

HRID 987598Notes

Reaction equation

HRID 987598 reaction equation
[OH:1][C:2]1([CH2:26][OH:27])[CH2:7][CH2:6][C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[O:11])[CH2:4][CH2:3]1.N1C=CC=CC=1.[CH3:34][O:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39]>C1COCC1.CN(C1C=CN=CC=1)C>[OH:1][C:2]1([CH2:26][O:27][C:38](=[O:39])[C:37]2[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=2[O:35][CH3:34])[CH2:7][CH2:6][C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[O:11])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 889692-Methoxybenzoyl chlorideHCID 18009504HCID 18009504, compound

Product 1

HCID 18009537HCID 18009537, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To solution of 1-hydroxy-1-hydroxymethyl-4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)-cyclohexane (Example 168, 20.2 mg, 0.055 mmol) in 2.0 mL of THF was added DMAP (2 mg), pyridine (0.054 mL, 0.67 mmol) and 2-methoxybenzoyl chloride (0.050 mL, 0.34 mmol). The solution was stirred at rt for 18 h and was quenched with methanol (0.5 mL). The volatiles were removed by vacuum and the residue was filtered through a plug of silica gel, concentrated and the residue was purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm) using a mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 3.0/9.0 to 8.0/0.0, mL/min) to give the separated isomers of the title compound.

Workup

  1. customwas quenched with methanol (0.5 mL)
  2. customThe volatiles were removed by vacuum
  3. filtrationthe residue was filtered through a plug of silica gel
  4. concentrationconcentrated
  5. customthe residue was purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm)
  6. additiona mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile

Sources & evidence

ORD record
ord-028a2bd60e624aec8f3f12aba41266d3
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

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