4-Methylmorpholine → HCID 86631572, compound

HRID 2363214Notes

Reaction equation

HRID 2363214 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH:19]([C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=3)[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:13][C:12]=2[CH3:33])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[NH2:53][CH2:54][C:55]#[N:56]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([CH3:33])=[CH:13][C:14]([O:18][CH:19]([C:24]3[CH:25]=[CH:26][C:27]([C:28]([NH:56][CH2:55][C:54]#[N:53])=[O:30])=[CH:31][CH:32]=3)[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:15][C:16]=2[CH3:17])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 11491918Aminoacetonitrile hydrochlorideHCID 67487767HCID 67487767, compound

Product 1

HCID 86631572HCID 86631572, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[1-(4′-tert-Butyl-2,6-dimethyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid (1.00 g, 2.25 mmol) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (593 mg, 3.38 mmol) is stirred in THF (25 mL) under nitrogen. N-Methyl morpholine (0.37 mL, 3.38 mmol) is added followed by addition of aminoacetonitrile hydrochloride (229 mg, 2.48 mmol) and the mixture stirred at room temperature for 24 h. The reaction is filtered and the resulting filtrate concentrated and purified by silica gel chromatography, eluting with hexanes using a gradient of 0-100% ethyl acetate to provide 806 mg (74%) of the titled compound as a white solid. 1H NMR.

Workup

  1. filtrationThe reaction is filtered
  2. concentrationthe resulting filtrate concentrated
  3. custompurified by silica gel chromatography
  4. washeluting with hexanes using a gradient of 0-100% ethyl acetate

Sources & evidence

ORD record
ord-0a599798e8bd47d083cad340562e6c77
Source dataset
uspto-grants-2014_04
Patent number
US08691856B2

Reaction notes

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