Cesium carbonate → HCID 58117336, compound

HRID 1406422Notes

Reaction equation

HRID 1406422 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]1[C:19](=[O:48])[N:20]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[CH:21]=[C:22]([NH:24][C:25]([C:27]2[CH:28]=[N:29][N:30]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[CH:31]=2)=[O:26])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl[CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:51][CH2:52][N:53]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]1[C:19](=[O:48])[N:20]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:47])[CH3:46])[CH:21]=[C:22]([NH:24][C:25]([C:27]2[CH:28]=[N:29][N:30]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[CH:31]=2)=[O:26])[CH:23]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 58117298HCID 58117298, compound2×

Product 1

HCID 58117336HCID 58117336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of intermediate (11e), 5-hydroxy-2-[5-{[1-(4-methyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]indole-1-carboxylic acid tert-butyl ester (150 mg, 0.22 mmol) in N,N-dimethylformamide (3 mL) was added 1-(2-chloroethyl)-piperidine hydrochloride (62 mg, 0.33 mmol) and cesium carbonate (219 mg, 0.67 mmol). The reaction mixture was heated at 50° C. for 5 hours, and cooled to ambient temperature. The reaction mixture was cooled and partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with brine, dried (Na2SO4) and concentrated in vacuo. The title compound was purified by flash chromatography on SiO2 eluting with dichloromethane—5% methanol/dichloromethane (gradient) to afford the desired title compound as a pale yellow solid, 94 mg, 54%.

Workup

  1. temperaturecooled to ambient temperature
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by flash chromatography on SiO2 eluting with dichloromethane—5% methanol/dichloromethane (gradient)

Sources & evidence

ORD record
ord-125ab110c7cd4dc0a31c70bd46fe4c93
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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