Potassium Phosphate, Tribasic → [3-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]propyl]-carbamic acid 1,1-dimethylethyl ester

HRID 2217816Notes

Reaction equation

HRID 2217816 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH:9]=[CH2:10])([CH3:4])[CH3:3].C12BC(CCC1)CCC2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([Cl:50])[C:36]=2[NH:40][C:41](=[O:49])[CH2:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[N:31]=1>O.CN(C)C=O.[Cl-].[Na+].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>[CH3:4][C:2]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][CH2:10][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([Cl:50])[C:36]=2[NH:40][C:41](=[O:49])[CH2:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[N:31]=1)([CH3:1])[CH3:3]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide

Product 1

HCID 86609738[3-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]propyl]-carbamic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2-propenyl-carbamic acid 1,1-dimethylethyl ester under nitrogen was added 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 7.1 mL) and the mixture refluxed for 2 hours. The reaction was allowed to cool to room temperature and potassium phosphate (1.02 g) in water (1.8 mL) added. The resultant mixture was stirred for 15 minutes. N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide (prepared as described in Example 1a) (0.5 g) was added followed by tetrakis(triphenylphosphine)palladium(0) (17 mg) in dimethylformamide (2.8 mL). The reaction was heated at 70° C. under nitrogen for 4 hours. To the cooled solution was added brine (30 mL) and the mixture extracted with ethyl acetate (3×30 mL). The combined organics were dried, filtered and concentrated to give the sub-title compound (0.9 g).

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. temperatureThe reaction was heated at 70° C. under nitrogen for 4 hours
  3. extractionthe mixture extracted with ethyl acetate (3×30 mL)
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-79cde24b823c469f8d8ebec26c7c0fc0
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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