Sodium Hydroxide → HCID 86586690, compound

HRID 2088157Notes

Reaction equation

HRID 2088157 reaction equation
[F:1][C:2]([F:35])([F:34])[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:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:17]([C:26]#[N:27])[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+]>ClCCl.O.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:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:17]([C:26]#[N:27])[CH2:18]3)[CH:4]=[C:3]([C:2]([F:1])([F:34])[F:35])[CH:8]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 69860Dimethylbarbituric acidHCID 86586689HCID 86586689, compound

Product 1

HCID 86586690HCID 86586690, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
32.5 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.011 mmol) was added to a stirred mixture of (1R*,2R*,5S*,7S*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-7-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane (Example 57; 68 mg, 0.14 mmol), 1,3-dimethylbarbituric acid (70 mg, 0.5 mmol) in dichloromethane (3 ml) at room temperature. The reaction mixture was stirred at 30-35° C. for 1 hour and treated with 2M aqueous NaOH (5 ml). The mixture was stirred for 5 minutes, then diluted 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 (37 mg, 60%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. stirringThe mixture was stirred for 5 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-0f624a0995b849bc9f4388b683311624
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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