Water → HCID 86586782, compound

HRID 2088231Notes

Reaction equation

HRID 2088231 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:21][CH2:20][C@H:19]3[N:22](CC=C)[C@:16]2([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:18]3)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CN1C(=O)CC(=O)N(C)C1=O.[OH-].[Na+].O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:21][CH2:20][C@H:19]3[NH:22][C@:16]2([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18]3)[CH:4]=[C:3]([C:2]([F:33])([F:1])[F:32])[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 69860Dimethylbarbituric acidHCID 86586781HCID 86586781, compound

Product 1

HCID 86586782HCID 86586782, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
32.5 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (97 mg, 0.084 mmol) was added to a stirred mixture of (1S,2S,5S)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane (Example 182), 1,3-dimethylbarbituric acid (270 mg, 1.9 mmol) in dichloromethane (10 ml) at room temperature. The reaction mixture was stirred at 30-35° C. overnight and treated with 2M aqueous NaOH (5 ml). The mixture was stirred for 30 minutes, then treated with water (30 ml) and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel to give the title compound (166 mg, 81% two steps). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionextracted into dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-71b2a2e92d2349faa062f7c8aea4961b
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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